All Forum Posts by: Kristen Ambrose

Great question. Once you hit five units, especially with short-term rentals, the volume of transactions and complexity really starts to pile up. Cleaning fees, supplies, OTA payouts, dynamic pricing, and multiple platforms all create noise if you do not have a system.

Here is what I recommend:

1. QuickBooks Online Plus or Advanced
   This allows you to track income and expenses by property using the Class feature. You can sync your bank and credit card feeds for automation and pull property-level profit and loss statements instantly.

2. Custom Chart of Accounts for STRs
   Set up categories that make sense for your business such as guest supplies, OTA fees, cleaning, and maintenance. Do not rely on the default setup. You will get much more insight when your books are structured properly.

3. Receipt Management
   Use a tool like Dext or Hubdoc. You can snap a photo of your receipt, tag it to the correct property, and push it directly into QuickBooks. It saves time and keeps everything organized for tax season.

4. Key Metrics to Monitor
   • Monthly cash flow per property
   • Expense categories as a percentage of revenue
   • Occupancy rate and average nightly rate
   • Net operating income
   • Owner distributions and reserve levels

5. Portfolio Dashboarding
   Once your books are clean and consistent, you can build a Google Data Studio or Excel dashboard using QuickBooks exports to monitor performance across your portfolio. You can also explore STR-focused tools like REI Hub if you want something ready to use.

If you are doing the bookkeeping yourself, make sure your system can grow with your business. If you want help getting set up properly, I run a bookkeeping firm that works exclusively with real estate investors and STR operators. Happy to help or answer any specific questions.

You're spot on that your current method will start to feel overwhelming as you grow. Many landlords start with spreadsheets and folders, but once you're managing multiple properties and doing flips, it’s time to put a system in place that scales with you.

Here’s what I recommend:

1. Move to QuickBooks Online (QBO) Plus or Advanced. You can set up each property as its own “Class” so you can track income and expenses by property. You’ll also be able to automate bank feeds, categorize transactions quickly, and pull reports with real insights.

2. Use a real estate–specific chart of accounts. Most generic templates miss key categories like rehab costs, security deposits, loan principal vs interest, etc. This structure is critical for getting clean financials and working efficiently with your CPA.

3. Stop saving receipts manually. Use a tool like Dext or Hubdoc that integrates with QBO. You can take a photo of a receipt on your phone, tag it by property, and the system will push it into QBO automatically with the right details.

4. Track flips separately. Flips need to be handled differently than rentals since they’re inventory, not long-term assets. QuickBooks can support both, but it’s important to structure your chart and process properly.

5. Get support from a bookkeeper who knows real estate. Most bookkeepers don’t understand HUDs, rehab draws, or cost basis. Having someone who speaks your language will save you time and help you make better decisions as you scale.

If you ever want a second opinion on your setup or help cleaning up the books, feel free to reach out. I run a bookkeeping firm that works exclusively with real estate investors and would be happy to point you in the right direction.

Great question. Keeping property level expenses organized is key, especially as you scale. Here's a simple and effective system that works well for real estate investors managing multiple properties:

1. Use QuickBooks Online with Class or Location Tracking
Set up each property as a Class or Location in QuickBooks. This allows you to tag every expense to the correct property, even if it's all coming from one bank account.

2. Upload receipts directly to QuickBooks
Use the QBO mobile app to snap photos of receipts on the spot. You can also email receipts to a unique QBO email address. Each expense can be matched to a transaction and assigned to a property.

3. Save receipts in Google Drive or Dropbox by property
Set up folders for each property. Within each folder, have subfolders like:

• Repairs and Maintenance

• Utilities

• Capital Improvements

• Contractor Invoices

This keeps your documentation organized and makes it easy to find supporting documents during tax time or when refinancing.

4. Track contractors and invoices separately
For 1099 purposes and cost tracking, enter contractor payments as expenses or bills in QBO. Always tag the property. If it’s a large rehab, you can even use Projects or sub-accounts to track by job.

5. Weekly or monthly reconciliation
Set a recurring reminder to review your transactions, match receipts, and tag everything properly. This avoids falling behind and helps catch issues early.

Clean systems like this give you full visibility into how each property is performing and keep you ready for tax season or a future sale or refi.

Congrats on the upcoming closing and house hack. You're making a smart move.

Here’s how to approach it:

1. Rent collection and lease signing
Use a platform like Avail or RentRedi. Both let you collect rent online, sign leases, and communicate with tenants. They’re easy to use and designed for small landlords.

2. Expense tracking
Use QuickBooks Online. It gives you full control over your financials, helps you stay organized, and makes tax time much easier. You can track income and expenses by unit or by property using class or location tracking.

3. Separate bank accounts
You don’t need a separate bank account for each unit. Just use one account for the entire property. What’s most important is keeping your rental finances completely separate from your personal accounts. You can track unit-level details inside QuickBooks without opening multiple accounts.

Congrats on the first property. You're thinking about this the right way.

Here’s a simple breakdown:

1. Create an LLC for the property
This provides liability protection and separates business finances from personal finances.

2. Apply for an EIN and open a business bank account
Each LLC should have its own EIN and dedicated bank account. All income and expenses should run through that account.

3. Build business credit
Start with a business credit card and vendor accounts that report to credit bureaus. Pay on time and keep usage low to build credit over time. This helps reduce the need for personal guarantees in the future.

4. Use one LLC per property
Keeping each property in a separate LLC helps isolate liability. If there's an issue at one property, the others are protected.

5. Consider a holding company
A parent company can own each individual LLC. This makes things easier to manage and can help with estate planning and financing strategy.

You're right to separate these. If you're using two different corporations, especially one in Honduras and one in Florida, you should not be using the same Airbnb account.

Airbnb only allows one account per phone number, but you need to set up two separate accounts. Here's why:

1. Taxes:
Each account is tied to one tax ID. If you use the same Airbnb account for both properties, Airbnb will send one tax form with all income under one name. That will create problems for your books and your taxes, especially if one is international.

2. Legal separation:
Each property is owned by a different corporation, so their income and expenses should be completely separate. Combining them in one Airbnb account could put that legal protection at risk.

3. Solution:
Set up a second Airbnb account with a different email, phone number, and payout method. Use a separate bank account for each entity and make sure the tax info in Airbnb matches the owner of the property.

If you want help making sure the finances stay clean and accurate for each entity, let me know. We work with a lot of investors running short-term rentals through different LLCs and holding companies.

Yes, I definitely recommend getting a credit card specifically for your STR business. Since you already have an LLC, it's smart to keep everything clean and separate. It makes taxes much easier and helps you avoid mixing personal and business expenses.

A separate credit card will make tracking and categorizing everything simple. It also helps if you're ever audited, and it makes it easier to see how your STR is performing. Plus, you'll be spending a lot upfront on furnishings and supplies, so using a card with rewards can give you points or cashback.

It also gives you some flexibility with cash flow during the setup phase and helps build business credit if you plan to buy more properties in the future.

You should look for a card that earns rewards on things like home improvement, travel, or general spending, and ideally one with no annual fee and good expense tracking tools.

One other tip is to track big purchases like furniture separately from regular expenses like cleaning supplies. Those larger items are treated differently for taxes. Also, make sure you have a bookkeeping system in place from the start, so everything is organized as you go. Let me know if you want help setting that up.

Hey I totally get where you’re coming from. A lot of investors start with Stessa but eventually run into issues once they grow beyond a few properties. The missing transactions, lack of customization, and poor reporting start to hold you back.

I know you mentioned you don’t need QuickBooks, but I work exclusively with real estate investors and run my own portfolio. QuickBooks Online is the best option once you’re serious about your numbers. It is the most widely used accounting software for a reason.

Here is why it works so well for investors with multiple properties:

• You can track each property’s performance in detail, including rent, rehab, cash flow, and loan payments

• It syncs with your bank and credit cards reliably, so you are not chasing missing data

• It makes tax season much easier because your CPA gets clean, accurate reports

• It grows with you, whether you have 7 properties or 70

I have worked with a lot of investors who felt the same way until they saw what was possible with the right setup. If you ever want to see what a real estate focused QuickBooks setup looks like, I would be happy to share.

Appreciate you sharing this. You are not alone. Many first-time investors start with the same questions. Here are a few thoughts to consider.

• You do not always need 20 percent down. Some second home loan products allow for as little as 10 percent down, especially if you plan to use the property personally throughout the year. These are different from investment loans and come with specific requirements, so make sure you work with a lender familiar with vacation markets.
• Yes, you can often borrow against your 401k, but be careful. If you leave your job or cannot repay the loan, the balance could be treated as a distribution and taxed. Talk to a financial advisor first.
• As for reserves, a good rule of thumb is to have at least three to six months of expenses set aside after closing. This includes mortgage, taxes, insurance, HOA, utilities, and any short-term rental management fees.
• AIRDNA is a great starting point, but you should also talk to local agents and property managers who specialize in short-term rentals in Santa Rosa Beach and Rosemary Beach. They can tell you which buildings have strong rental histories and which have restrictions.
• If your goal is to break even, make sure you account for seasonality. Income can vary significantly month to month in beach markets.

It sounds like you are taking the right steps by educating yourself and asking questions. The first purchase is always the hardest, but each step gives you more clarity and momentum.

Great breakdown. As a CPA and investor, I have been thinking through many of the same questions with my clients.

A few things I am keeping a close eye on:

• Bonus depreciation. If it phases out faster or gets limited, modeling ROI on flips and BRRRRs becomes more challenging. Planning ahead for capital expenses is even more important.
• Entity structure. If pass-through benefits change, it could shift the balance between S-Corps and LLCs for active investors. We have already had to rethink how cash flows between entities.
• Cost segregation studies. I actually think these might become more urgent to complete now while the current rules still apply. Waiting could mean leaving value on the table.

I am encouraging investors to run a few “what if” models now instead of waiting, especially if they are scaling, taking on new debt, or holding assets long term.

Curious to hear how others are planning around this. Has anyone started adjusting strategy yet?