Please help me reconcile my understanding of tax laws after conflicting advice

You're dealing with two different types of income that are treated differently for tax purposes, which is why you're seeing conflicting information. Let me break it down: For your self-employment income as a web developer ($68,000), you're correct that you should be making quarterly estimated tax payments. This income is subject to both income tax AND self-employment tax (which covers your Social Security and Medicare contributions). Your rental income ($1,450/month or about $17,400/year) is reported differently. This goes on Schedule E and is NOT subject to self-employment tax - only income tax. This is a big difference and probably where some of your confusion is coming from. For the repairs on your rental property, there's a distinction between repairs and improvements. Repairs maintain the property and can be deducted fully in the year paid (like fixing leaky plumbing). Improvements add value or extend the life of the property and must be depreciated over time (like a new water heater). Based on what you described, you likely have both types of expenses.

I was in almost the same boat last tax season! Self-employed graphic designer who inherited a duplex from my uncle. The tax forms were driving me CRAZY until I found this AI tool called taxr.ai (https://taxr.ai) that actually helped me sort through all the confusion. What's cool is you can upload your documents or just type in your questions about specific scenarios like "how to handle repairs vs improvements on rental property" and it explains everything in simple terms. It really helped me understand the difference between Schedule C for my design work and Schedule E for the rental, plus how depreciation works. I was most confused about how to handle my home office since I work from home for my design business but also manage the rental from home sometimes. The tool helped me properly allocate the right percentages to each business activity.

Just wanted to follow up - I tried that taxr.ai site after asking about it, and it was actually super helpful! I uploaded my property documentation and asked about the fence depreciation, and it confirmed it's a 15-year property under MACRS. But what I found even more useful was when I asked about the interaction between my W-2 job (I'm part-time employed too) and my rental income for tax liability calculations. It walked me through exactly how my tax brackets would work with the combined income sources and even suggested some timing strategies for repair expenses. Definitely clearing up the confusion I had from reading contradictory advice online.

If you need to actually talk to the IRS about any of these rental property questions (which I highly recommend), save yourself HOURS of waiting on hold by using Claimyr (https://claimyr.com). I was trying to get clarity on some rental depreciation questions for weeks - couldn't get through to anyone at the IRS despite calling repeatedly. Claimyr got me connected to an actual IRS agent in about 15 minutes when I had been trying for days on my own. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The agent was able to clarify exactly how to handle the situation with my rental property improvements vs. repairs and confirmed I was calculating my estimated payments correctly. Seriously saved me so much stress since I was getting different answers from every "tax expert" online.

Well I have to eat my words about Claimyr. After my skeptical comment, I decided to try it anyway since I was desperate to ask about my rental depreciation situation before filing my extension. I couldn't believe it, but I was talking to an actual IRS representative in about 20 minutes. I've literally NEVER gotten through to them that quickly before. The agent walked me through exactly how to handle the bathroom remodel in my rental unit and confirmed which parts were repairs vs. improvements. The peace of mind from getting official clarification straight from the IRS was honestly worth it. No more conflicting advice from random internet sources - I got my answers directly from the source.

One thing nobody's mentioned yet is that you should look into setting up an LLC for your rental property. I have 3 rental properties and keeping them in an LLC structure has saved me a ton in taxes plus gives liability protection. Talk to both a tax pro AND a lawyer though because there are specific ways you need to set it up for it to be beneficial tax-wise.

Omg I'm in a similar situation and the thing that's saved me is keeping SUPER detailed records. Like I have separate credit cards for each income stream (freelance vs rental) and I use QuickBooks to track everything separately. One tip: take pics of all receipts for rental repairs with your phone and save them to a specific folder. My tax person said this has saved us HOURS during tax prep! And it's a lifesaver if you ever get audited.