W2s and financial statements are arriving in the mail. It’s time to submit your taxes. We file our own taxes. And that surprises people every year.
We have 12 rental properties, two of which are owned with a partner. Mr. ODA works full time. I work random jobs, but produce income that requires filing. This sounds like it can be complicated, but it’s not.
Mr. ODA projects out our tax liability all year long, and he makes adjustments in his W2 paycheck to account for what we’ll owe. Our goal every year is to owe. Our philosophy is that if we get money back, that’s just an interest free loan the government has had from us all year. I can make a whole post on how getting excited for a tax return shouldn’t be a thing, but I’ll just leave it at. But you can’t owe too much, because then you have to pay a penalty. It’s a careful balance that I entrust Mr. ODA with and don’t ask any questions.
This post focuses on having business-type expenses. If you file just W2 income, then it’s not something you need to manage all year long, but you can still do your taxes on your own!
BUSINESS EXPENSES
The key to getting through tax season is knowing that it takes work all year long, not just in the one week crunch time to file your taxes. Schedule E is going to require you to put your income and expenses, per property, not as a whole, so it’s important to have expenses assigned to a particular house. If you record income and expenses as they occur, it’s less of a hurdle when the year is over. By recording the activity all year, it then becomes a verification process when the year is over, thereby reducing the possibility of missing something or recording something wrong.
At the beginning of every year, I create an Excel workbook to track each property’s expenses. I use it as a projection of income, a projection of expenses, and a way to keep track of re-occurring expenses (e.g., stormwater utility bills I can’t assign to the tenant for payment). I set up each property on a separate spreadsheet within the workbook to identify all known costs for the coming year.

Not all of these categories apply to each property (e.g., HOA, prepaid points), but I found it was easier flipping between each spreadsheet if they were uniformly set up. There’s also a chance that you’re carrying appliance depreciation costs. Appliance purchases aren’t captured as a one-time cost in the year of purchase; the purchase is required to be depreciated over its useful life (e.g., a $500 dishwasher purchased on January 1 is depreciated over 5 years, so it’s $100/year worth of an expense claimed on your taxes). As I incur expenses or need to adjust my income, I record it per property.
After the end of the year, I then verify what I’ve recorded. I make sure that I have the right income for each property (e.g., were there late fees collected, were there rent concessions granted, were there non-payments). Then I go through each property’s paper folder I have filed to make sure I’ve recorded anything I have a receipt for. Then I go through my electronic folder for each property, and this is where nearly all my record keeping is (e.g., I have Lowe’s and Home Depot automatically email me receipts for a purchase, and all my contractor work is billed via an invoice emailed to me). I’m verifying that I have a receipt for any expense that I incurred and recorded already. I’m also verifying that I haven’t missed recording an expense that I have a receipt for.
Once I have everything verified, I let Mr. ODA know that the business expenses are ready. Inevitably, we’re waiting for some final investment account documentation to be available before we can input our data, but we’re mostly ready to go.
TAX SOFTWARE
Each year, we hunt for deals on websites that will allow us to pay nothing or a minimal cost for filing our taxes. We’ve spoken to a couple of financial people to see whether having a CPA do our taxes would be better, but they always agree that inputting in Schedule E is the only way to go, which is really straight forward. If we’re trying to not pay to file our taxes online, then we don’t want to pay someone to enter the data on our behalf if they’re providing a benefit outside of that. I know several people who use a tax accountant to file their taxes, and they rush around looking for all their documentation to provide that person. That seems more overwhelming to me, and it just seems faster to be on top of it myself than gathering receipts and being ‘on call’ to answer questions.
Filing our taxes is usually a 2-3 hour process. It’s not complicated, but it’s time consuming. We’ve found the best way to do it is having Mr. ODA input the data, as I pull the information he needs. I keep a tax folder to file all the paperwork we receive around this time of year (mortgage statements, investment account statements, etc.). I have that file handy, as well as all our account log-ins. I’m trying to pull information as fast as I can while he’s entering it and clicking through the software. Sometimes there’s something that trips us up because there seems to be a change each year, but we mostly have a groove by now.
If you haven’t filed your taxes on your yet, take this as a sign to give it a try!