Spent 20+ hours hunting receipts for my accountant - how do YOU handle tax prep?

Question

Hi folks,

I manage 10 units (CA + FL) with a full-time software job.

This Oct, tax prep took me 20+ hours - basically 2 entire weekends, after a lot of procrastination. I already pay for CPA and still feel like I am doing a lot myself. Here's my current "system":

- Photos on my phone (some from 8 months ago)

- Paper receipts in a shoebox

- Some expenses in Google Sheets (when I remember)

- Random Venmo/Zelle I can't explain

My accountant asks "How much did you spend on plumbing at the Florida property?" and I'm digging through bank statements for 30 minutes.

Questions for those who manage multiple properties and/or juggle several hustles:

- How many hours does tax prep ACTUALLY take you?

- How do you track expenses throughout the year?

- Do you log receipts immediately or batch them monthly?

- Any tools that actually save time vs just organizing the chaos?

Honestly, This is why I haven't bought property #11. I literally don't have the time for more admin work, and infact considering reducing my portfolio.

What am I missing?

Thank you,

Gaya Sandeep

John Morgan · Answer

I do my taxes for my 31 rental properties on turbo tax. It’s pretty easy to do. I have a folder for each house and write down the expense then jam a receipt in the folder. It takes two seconds. Then I plug the expenses in for each property at tax time. I’m a little old school but it works and is quick.

Jake Baker · Answer

@Gaya Sandeep

At the bare minimum, you should do the following to make your bookkeeping easier:

Dedicate one checking account and credit card exclusively to real estate. Keep personal and business finances separate to create fewer headaches.

File all receipts in a dedicated Google Drive folder. Digitize physical receipts for easy storage and use a consistent naming convention for easy sorting.

Maintain proper records, such as contracts, settlement statements, and promissory notes.

Additionally, you can track income and expenses consistently using software or spreadsheets. I agree with @Aaron Zimmerman that QuickBooks Online is my software of choice. I use QBO for my flipping business, rental portfolio, and bookkeeping clients. QBO has every feature you need to run a business, excellent reporting features, and integration with other software. It is the most popular software in the industry, and most Tax Preparers are familiar with it, which makes tax season easier.

As you scale, if bookkeeping isn't fun, consider hiring a bookkeeper for a couple of hundred bucks per month. This is often one of the first things a real estate investor will outsource to save time and headache. Many bookkeeping companies are not worth the money, so vet them carefully, and make sure they are real estate-focused if you do.

Aaron Zimmerman · Answer

As a cpa that does tax prep and I invest myself, bookkeeping can be a pain, for sure.

I think at your stage, you want to be moving to a tool like quickbooks. You'll want to track each property separately (which are classes in qb). You'll also want to do your bookkeeping on a monthly basis (classify transactions and do monthly reconciliations for banks and credit cards). Depending on how much activity there is, for 10 properties, I could see this being 5-7 hours a month and ideally less when you get the system going.

an advantage of using a system like qb is that you can also attach receipts as well so you don't have them in so many different places.

if you maintain your records, ideally tax time will be a breeze. Another bonus of having up to date bookkeeping is that you'll actually be able to do tax planning.

Marcus Auerbach · Answer

Same drama, bookkeeping has always been a painfull thorn in my side!

At some point I hired a service do to my books and that was one of the best decisions ever. I am just not cut out for it, I honestly resent doing it and as a result procastinate. So hiring a service was one of my best decsions ever. It made my quality of life better and I am not even exaggerating.

My boookkeeping servcie has access to all my bank accounts (view only) and they reconcile accounts with income, expenses and credit cards. We have also streamlined our operations: we only pay via check or credit card, period. We only use dedicated accounts. If you have to look for an expense in four different systems it's hard, if you have account discippline and there is only one account you use to pay for rehabs, it makes searching MUCH easier.

Having a bookkeeping service also helped us create the necessary discipline, because every time I would budge and pay a contractor with paypal now I have to explain to my BK what the heck happened. So I don't, not an option.

We have 2 folders for the businesses permanently set up in our mudroom, that's where receipts go. I also have a fast (more expensive) laser printer in my office - this seems silly, but when printing a receipt would cost me 30 seconds vs 5 seconds I would often mark the email unread to leave it for "later". Now it takes 5 seconds. And so I print it right away, which helps with zero inbox. Also better for my life. Receipt folders get dropped off about every 2 weeks on my way to the office (and not on the other side of Milwaukee where I would need an extra drive) and then our BK has a updated quickbooks file for me at the end of each months (I have onlien access) so I can look at the reports and have near real time data.

Around tax time the BK talks to my CPA - very little work for me.

James Jones · Answer

Gaya, I’ve been there. Once you get past a handful of units, “shoebox plus screenshots” stops working, and tax prep becomes a full-weekend scavenger hunt. I manage a large portfolio now, and tax prep takes me less than an hour because everything is organized as the year happens, not at the end of it.

Here’s what actually works in real life when you’re juggling multiple properties:

Use one system for all transactions

Whether it’s QuickBooks, Stessa, or Buildium, the key is that every income and expense flows through one place. No Venmo randomness, no mystery Zelle transfers. If it’s not trackable, it didn’t happen.

Automate 90 percent of categorization

Bank feeds categorize recurring expenses automatically once you teach them.

PM fees, mortgages, utilities, insurance, landscaping, etc. should all auto-classify.

The only manual entries should be one-off repairs or CapEx.

Log receipts immediately

I snap a photo and upload it directly into the accounting app.

Five seconds now saves an hour later.

The people who batch receipts monthly usually fall behind once they hit busy season.

Schedule one 30-minute admin block per week

Not for “paperwork,” but for:

reviewing transactions

matching receipts

tagging anything that needs clarification

That’s it. If you touch it weekly, tax prep becomes a non-event.

Your accountant should never ask you to dig through bank statements

That’s a sign your data isn’t categorized consistently. When everything lives inside one accounting system, they can pull reports instantly: plumbing by property, CapEx vs repairs, mileage, management fees, depreciation, everything.

Actual time spent on tax prep once your system is clean

For most investors I mentor:

Under 2 hours if records are well maintained

Under 1 hour once automation is fully dialed in

The CPA should be doing the heavy lift, not you.

You’re not missing anything. You just need one source of truth and a weekly cadence. Once you clean up the workflow, adding units feels the same whether you own 5 or 25.

Scott Brockelbank Jr. · Answer

I track all my expenses monthly. Takes about an 30min-1 hour  to download my cc statement and organize my receipts in one spreadsheet. Make this part of your routine, pay all your water bills and then do your expenses type routine. There are plenty of softwares that will do this for you and probably can connect to your rent collection. I have 8 units today and doing it monthly is very manageable in a spreadsheet but I can see upgrading to a buildium in the future.

my question for you is how do you know how your properties are performing throughout the year if this isn't easily accessible?

Basit Siddiqi · Answer

I would suggest the followingSave all your receipts in some online storage(I.E. Google Drive, Dropbox, Apple Drive, etc)Organize all your information in excel(if you don't want to move to an accounting software).I would create separate columns for the following information regarding to your receiptsA) DateB) AmountC) VendorD) PropertyE) ClassificationIf you forward this to your accountant, he should be able to complete the return on his own. Best of luck!

Jules Aton · Answer

I track material participation hours but am a receipts in a box person until January when I scramble. TBH if you are only spending 2 hours per property that doesn't sound like an unreasonable amount of time each year.

Mark F. · Answer

Maybe someone already mentioned but I have 7 units and this is what I do. I spend maybe an hour a month total I guess. Google Sheets that I can access from my phone and computer. Soon as I have an expense (talking repair, maintenance or utility charge), I open my phone and log it immediately. I found a template somewhere online that is great and has all the stuff I need. Each property has its own excel file. Date, expense category, amount, short description (now I include which unit), mileage if applicable.

For mortgages, I usually log those at the end of the year. Takes maybe 30 minutes and it’s minor adjustments since I make a new copy for the new year so the principal and interest are only off a few bucks every year. I can do the find and replace feature for rent increases. This also helps me project future CF with rent increases since maintenance items and utilities are already estimated, I just copy and make a new one for the next year.  Never had a complaint from a cpa. If you want a copy template just shoot me a message.

The biggest time save is doing the maintenance and repairs immediately. Since I copy from last year the vast majority of the work is done. Is it completely hands off? No. But I save some cash from using a bookerkeeper and Im hands on so I know where everything is going. I have one CC and one bank account for the rentals so I see everything.

Edit- I read your post where you write stuff down. The key to my success is using my phone with Google Sheets. It doesn’t matter how I pay someone (cash Venmo etc) because soon as I do, next step is to open Sheets and log it. I don’t need to remember to do anything and we always have our phones on us.

Gaya Sandeep · Answer

Thank you so much for all the responses. I’ve been more of a passive member here, and it’s great to see how engaged and helpful this community is.

TBF, I’m disorganized, and extremely busy juggling a day job and kids (or simply - I procrastinate these things :)) — so there’s definitely room for improvement in how I track things. For the properties that use PMs, I get monthly statements and usually just do “napkin math” to gauge performance, but it’s not consistent; and doesn't cover everything right (mortgage, insurance etc.). And I know bookkeeping needs to be accurate, not approximate.

Another aspect where I struggle is reconciliation. Sometimes I pay vendors via Zelle/Venmo, and for small handyman work I pay cash. I jot it down somewhere… but retrieving it months later isn’t always smooth. That’s part of why tax prep or even for my own accounting purpose turns into a 20-hour hunt.

I'll also probably DM to know more, but a few follow-up questions for anyone willing to share more detail about your actual workflows 1.  For those who batch everything monthly or do a End-of-year/January scramble, what does that process look like step-by-step? What typically slows you down?

2. If you’re saving receipts to cloud storage or spreadsheets, which parts take the most time or tend to fall behind?3. Quickbooks felt like a heavy hammer approach (expensive, and not sure of ROI) for my size of portfolio, maybe can you tell what pushed you to move away from the receipts-in-a-box method?

4. And for tracking material participation hours and not receipts, what makes the receipts piece harder to stay consistent with?

Spent 20+ hours hunting receipts for my accountant - how do YOU handle tax prep?

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