Should You Hire a Bookkeeper or Do It Yourself? A Real Estate Investor’s Guide (For Flippers & Landlords)

Whether you're collecting rent or cashing in on a flip, there’s one part of real estate investing that everyone underestimates: bookkeeping.

At first, it’s tempting to keep it all DIY—especially if you're only managing one project or property. But as your business grows, your books can quickly become a time-consuming mess, or worse—flat-out wrong.

So how do you know when it's time to hand it off?

Let’s break it down for both flippers and rental property owners.

DIY Bookkeeping Might Be Right If…

✅ You only have one or two properties or flips at a time.

At this stage, it’s manageable to track things yourself—especially with tools like spreadsheets or Stessa.

✅ You’re organized, disciplined, and enjoy managing your finances.

If you like numbers, understand tax basics, and stay consistent each month, DIY might work—at least for now.

✅ You have time to learn real estate-specific accounting rules.

Both flips and rentals come with unique tax rules (e.g., capital improvements, holding costs, depreciation, etc.). If you’re up for the learning curve, DIY could still be a solid option.

You Might Need a Bookkeeper If…

🚩 You’re falling behind or avoiding your books.

If your books are always “a little behind,” or you haven’t looked at them since last quarter, it’s probably time for help. That backlog gets expensive.

🚩 You’re doing multiple deals at once.

Whether it’s:

• 4 flips with overlapping timelines, OR

• 6 rentals with different rent due dates, lenders, and repairs...

The volume adds up fast—and DIY gets risky.

🚩 You're unsure which expenses are deductible—or how to track them.

Flippers need to separate direct costs (labor, materials) from capitalized costs. Rental owners need to split repairs vs. improvements. If you’re guessing, you're likely missing deductions—or miscategorizing them altogether.

🚩 You're making decisions without reliable numbers.

You can't measure ROI, profit per deal, or cash flow without accurate books. If you’re unsure what your numbers really say, you’re flying blind.

Why Flippers & Landlords Need Different Bookkeeping Setups

Bookkeeping for flipping houses isn’t the same as for buy-and-hold rentals. Here’s how they differ:

Category	Flippers	Landlords
Revenue	One-time sale	Ongoing rental income
Expenses	Project-based (materials, subs)	Recurring (mortgage, repairs, mgmt)
Tracking	Cost of goods sold, project timelines	Depreciation, cash flow, cap ex
Bookkeeping Risk	Misclassifying flip costs can blow your taxes	Ignoring depreciation or repairs can kill deductions

That’s why your bookkeeping system should match your investing strategy.

🌱 How We Can Help

At Seeds, we work with both flippers and landlords who want their books to grow with their business.

Here’s how we support you:

• Fresh Growth Setup For investors who want to DIY with a strong foundation. We build your system—so you don’t have to guess.

• Weed Out Service Messy books from a busy season or several flips ago? We untangle the chaos and get you caught up.

• Blossom Bookkeeping Our full-service option—perfect for investors who want to stay focused on deals, not data entry.#
  

Final Thoughts

Whether you flip houses, hold rentals, or do both, bookkeeping is one of the least glamorous—but most important—parts of your business.

So ask yourself:

• Am I consistent?

• Do I understand what’s deductible?

• Are my books helping me make better decisions—or just stressing me out?

If it’s the latter, it might be time to call in help.

👉 Curious what it would look like to hand off your bookkeeping? Let’s chat. We’ll figure out the best path forward for where you are now—and where you’re growing next. Book a Call Today!