How Hilton Head Properties Realty & Rentals Closes Its Books 80% Faster

Lillian Robbins has spent eight years managing accounting services for Hilton Head Properties Realty & Rentals, a family-run vacation rental management company that owners Darcey and Terry Sundling have grown to 132 properties across a 12-mile stretch of Hilton Head Island, South Carolina. 

Over the last three years, the company invested in its tech stack, adopting Streamline as its PMS, QuickBooks Online as its accounting software, and Breezeway for operations. Their expense tool tracked expenses well. But for Hilton Head Properties, closing the books still meant manual work behind the scenes, a gap that left Lillian spending a week every month bridging it herself. That gap is what led them to Topkey.

The Challenge: Disconnected Financial Operating System

Before Topkey, Hilton Head Properties Realty & Rentals ran its expense management through Accountable, a tool that got the company off pure manual receipt tracking, a real step forward at the time. It did integrate with Streamline, QuickBooks Online, and Breezeway, but for Lillian, those integrations still meant manual work and workarounds to close the books. That gap is what left Lillian doing hours of manual re-entry, multi-day reconciliations, and chasing down receipts to make sure everything made it into the books.

Streamline sync that still meant manual re-entry

Their past tool did sync data to Streamline, but every transaction still had to be manually re-keyed by hand to actually make it accurate and billable. Lillian said flatly that this manual entry was "the bulk of the work, actually," days and days of entering billing information into Streamline, one line at a time, no matter how many transactions their software had already logged.

QuickBooks reconciliation that landed in one lump account

On the QuickBooks Online side, it was worse. Lillian called it "extremely hard" to reconcile because the previous system, for reasons she could never quite pin down, never matched up cleanly with their chart of accounts. Instead of syncing to the correct expense line, everything landed in a single lump GL account, leaving her to manually sort every transaction into the right category herself, a process she called "a project by itself" that regularly stretched across multiple days.

Breezeway integration that stayed manual

Getting labor and material charges from Breezeway into Streamline stayed a manual, job-by-job process. Terry tagged each completed job as materials or labor inside Breezeway, then flagged bills to Lillian one at a time as they came in, "Lillian, by the way, here's another bill," rather than in one batch. From there, Lillian had to comb back through Breezeway's tags herself to reconstruct what needed to be billed as labor versus materials, then key every one individually into Streamline, a process that repeated for every one of the 75 to 125 work orders the crew logged each week.

Advance statements, a project of their own

On top of the account cleanup, reconciling advance statements, tracking owner funds held ahead of upcoming stays, was a second, separate project every month. Asked how much extra time that took, Lillian didn't hesitate: "Oh, you don't want to know. That was a project by itself every month when I was reconciling advance statements. Days, yeah, days."

Receipts that didn't always make it

The problem went deeper than integrations. Field receipts uploaded from a phone in the truck would sometimes silently fail to save to their previous tool's server, and the team wouldn't find out until the end of the month, when the documentation simply wasn't there. Terry, who runs field operations, remembered it clearly: "You would take the photo, you would upload it, and then the end of the month would come along and it's not there."

The fix the crew came up with wasn't a policy change, it was a habit: technicians started taking two photos of every receipt, one for the app and one saved directly into Breezeway as a backup. Terry Sundling put it simply: "It just didn't have the integrations you guys have. It didn't have the platform to integrate over everything as easily as Topkey does."

For a company running 132 properties, that gap meant the tool built to save time was quietly creating more of it. Across 75 to 125 work orders a week, the manual entry added up to roughly 5 hours a day for the first two weeks of every month, racing a hard deadline to close the books by the 15th. Underneath it all sat something harder to schedule around: real uncertainty about exactly how much money was moving through the business. Closing that gap is exactly what Topkey was built to do

The Solution: One System That Automates the Whole Financial Workflow

Topkey rebuilt the entire flow, from the moment a technician swipes a card in the field to the moment it lands in the P&L. The crew doesn't hold onto receipts, Terry doesn't chase down bills, and Lillian doesn't key any of it into Streamline or QuickBooks Online herself.

A system the whole crew could run

1. Flexible corporate cards

Topkey gives STR operators the flexibility to use whatever cards make sense for them. Hilton Head Properties Realty & Rentals chose to run Visa and American Express, including an American Express card kept specifically for Amazon purchases. That choice now earns them 5% back in rewards, an option they didn't have with their old provider. On $100,000 in purchases, that's $5,000 back, money that would have otherwise gone unclaimed.

2. Receipt tracking you can trust

Every technician on the crew now carries a connected card and pays directly at the register, no personal reimbursement, no receipts stuffed in a truck door pocket, and no risk of a photo quietly failing to save the way it used to. Terry describes what that removed for his team: "It's the love of having not to worry about my guys having to save every single receipt every time they come through this door."

The step that replaces all that saved paper takes seconds, not a sit-down session. "They're able to go click, click, click," he says, "and they can keep moving during the day." That speed is what got the crew to adopt it without a fight. They didn't have to learn a new system, they just kept working the way they already worked in Breezeway, with one extra tap.

3. A single weekly handoff

Topkey turned Terry's side of this into one weekly pass instead of a running string of messages. "I go through every bill every week on Breezeway to make sure everything is proper and then push it over to Lillian so she's got it," he says. Instead of interruptions landing on her desk throughout the week, she gets one clean, sorted batch she can process in a single sitting.

Connecting the financial stack

1. Streamline integration that just works

Before Topkey, entering billing information into Streamline meant days and days of manual work, one line at a time. Now, as Lillian describes it: "I just go in there and I sync them and that's it, done." What used to be the most time-consuming part of her month now takes minutes.

2. A Breezeway process with no manual steps

Breezeway work orders now upload directly into Topkey, and Topkey syncs that data into Streamline on its own. Where entering billing information used to eat up days at the start of every month, Lillian now sets aside about an hour a day to post everything from Topkey into Streamline. "As long as the information is in Breezeway, I can get it done quickly," she says. "It takes no time whatsoever, compared to the way I was doing it prior."

3. QuickBooks Online, without the lump account

Under the old system, every transaction landed in one lump GL account, and Lillian had to comb through it by hand every month to sort it into the right expense categories, work she called "extremely hard" because the two systems never matched up cleanly. With Topkey, that sorting happens automatically. "The accounts are there," she explains, "so when I sync to QuickBooks Online, it automatically goes into the expense account the way it should." That same fix closed out both of the monthly projects the old tool used to hand her: the lump-account reallocation and the separate advance-statement reconciliation. Neither is something she has to sit down and untangle anymore.

The Results: Time Savings, Revenue, and Control

With the field, the back office, and the books finally pulling from the same data, the two weeks Lillian used to lose every month during close shrank down to days, and the numbers back it up.

40+ hours a month back

Closing the books used to take Lillian roughly 5 hours a day for the first two weeks of every month, the price of manually keying in transactions and untangling thier previous lump account before the 15th deadline. That same work now takes her about an hour a day. Add the shift up across a single month, and Lillian describes it best herself: "You're probably talking almost a 40-hour work week by the end of a month." For someone whose job already reads accountant, bookkeeper, HR, and payroll in the same breath, getting a full work week back inside a single month changes what the rest of her time is for.

An 80% faster close

Two weeks a month, 5 hours a day, 10 working days: that put Lillian's old close at roughly 50 hours, every month, before she could even confirm the numbers were right. Now, at about an hour a day across the same stretch, the close runs closer to 10 hours, an 80% drop in the time it takes to get from raw transactions to confirmed books. The business impact isn't only the hours saved. It's what happens on the other side of the 15th: owner statements go out on schedule instead of under a scramble, and the deadline that used to define two weeks of Lillian's month barely registers anymore.

Work orders that pay for themselves

Every work order that runs through Breezeway gets tracked, timed, and billed at a set labor rate, currently $65 an hour for repairs, with a small incentive bonus for the crew each time they cross $1,000 in tracked hours in a week. That tracking used to be an afterthought. Today it's precise enough that Terry can point to exactly what it added up to. "Just the revenue from labor generated paid for one of the guys," he says. "Wholeheartedly. Just paid for one employee." For a company already running lean, that's not a rounding error. It's a second business case for a process most companies treat as pure overhead.

Real visibility into where the money's going

Before Topkey, knowing exactly how much money was moving through the business day to day was mostly a feeling, not a fact. Now the team reviews real numbers every Monday in a leadership meeting built around scorecards pulled straight from the data. One week might show $715 in tracked labor charges, the next $1,490, and instead of shrugging at the swing, they use it to ask real questions: why the jump happened, where they should put more time, and which jobs make more sense to send to outside vendors instead of handling in-house. It's a different kind of result than hours saved or dollars recovered. It's the difference between running the business on instinct and running it on data.

Busy season, without the pile-up

The team made the move to Topkey in March and April, right before their busiest stretch of the year, the moment most companies would call the worst possible time to switch platforms. Looking back, Lillian called it the opposite: "It was a lifesaver for us."

Under the old system, a busier month meant more manual work, plain and simple: more work orders meant more tag-searching, more one-by-one entries, more hours. With that work automated, volume and workload aren't tied together anymore, so the busiest months don't hit the back office the way they used to.

No longer playing catch-up

For most of the last eight years, the two weeks Lillian spent closing the books each month were two weeks everything else waited: tax documentation, reconciliation backlogs, employee PTO records. Now she's finally working through that backlog instead of just staying ahead of the next deadline. "Those are things that I'm catching up on right now that Topkey is allowing me that flexibility with time," she says, pointing to the annual tax documentation her accountants now request. Instead of scrambling when they ask, she has it ready: "So when they do, hey, it's right here. I don't have to say, I'll give it to you next week.”

Why Topkey?

Terry put it best: "I think that trying to compare Accountable to Topkey at this point is not exactly apples to apples. I mean, it's just not the same platform... Are you able to track your charges and have everything photographed and have a documentation of it? Yes, but not having that next step that integrated Breezeway along with it to make the billing process easier into Streamline, that was the huge difference." The two tools were never solving the same problem.

What Hilton Head Properties Realty & Rentals needed was a system that carried that data all the way through to a closed set of books, without Lillian re-keying transactions, untangling a lump GL account, or chasing down missing receipts every month. That's what led them to Topkey.

The software wasn't the only reason it stuck, though. Lillian points to the people behind it just as quickly as the platform itself. "I mean, we had a lot of support," she says. That support showed up as more than a help line. The team got hands-on guidance through onboarding, clear expectations set up front, and reassurance heading into a summer launch that most companies would have pushed to the off-season.

As Darcey put it, "A lot of hand-holding through the process... they set us our expectations... they reassured us that they had our backs." For a company nervous about switching platforms mid-summer, that reassurance mattered as much as any feature on the roadmap.

The Ceiling Isn't the Bookkeeper, It's the System

Two years ago, adding another property meant more manual entry with no efficiency gain to show for it, work that landed squarely on Lillian's desk no matter how busy the season got. Today, when the team at Hilton Head Properties Realty & Rentals talks about adding another 50 units, the hesitation isn't about the books. "I think we could scale off of what we're working with right now," Terry says.

That's the real measure of what changed. The tool that once left Lillian doing the work software should have done now runs quietly in the background, and the two weeks she used to lose every month finally belong to her.

Most teams just accept that closing the books takes what it takes. Hilton Head Properties Realty & Rentals didn't, and got a week's worth of time back every month for it. See what Topkey could do for your team. Book a demo today.