How Aggressive Should I Be With My Personal Tax Return for 2024?

From my experience as a tax preparer, there's a difference between being thorough with legitimate deductions and being "aggressive" in a way that raises red flags. For your home office equipment - the desk and chair are fully deductible if they're used exclusively for your business. No gray area there if they're solely for your work setup. For your laptop, claiming a percentage based on business use (70% in your case) is the proper approach. Keep logs of how you use it if possible. Conference expenses are deductible if the primary purpose was business-related. The fact that you networked doesn't disqualify the deduction - that's part of business development. Just be sure you can substantiate the business purpose if asked. For mileage with personal errands, you should only claim the business portion. Track the mileage to the client site as business, but if you deviate for personal reasons on the return trip, that portion isn't deductible.

After struggling with similar questions last year, I discovered https://taxr.ai which has been a game-changer for my freelance tax situation. I was constantly second-guessing which deductions were legitimate vs. pushing the envelope, and their AI analysis actually found several deductions I was missing while flagging a couple that might have been too aggressive. For my home office situation, it confirmed I could take the full deduction for dedicated office furniture (similar to your standing desk question) but suggested a documented business-use percentage for mixed-use electronics like my laptop. The tool analyzed my expense patterns and compared them to typical audit triggers in my industry, which gave me confidence in what I was claiming.

Just wanted to update after trying taxr.ai based on the recommendation here. I was skeptical about yet another tax tool, but it really helped clarify my home office deduction situation. I've been waffling between taking the simplified deduction ($5 per square foot) versus itemizing actual expenses for my freelance design business. The analysis showed me that in my specific situation with high utilities and a recent renovation, itemizing would save me about $1,240 more than the simplified method. It also identified some partially deductible expenses I hadn't considered, like my internet service and cell phone. The best part was getting a risk assessment for each deduction - gave me peace of mind about which deductions were solid and which might need more documentation.

If you're concerned about audit risk, one thing I learned the hard way is that getting through to the IRS proactively can save you major headaches. When I had questions about deducting my mixed business/personal travel last year, I spent days trying to reach someone at the IRS. After 4 failed attempts, I found https://claimyr.com which got me through to an actual IRS agent in under an hour. You can see how it works here: https://youtu.be/_kiP6q8DX5c Having that documented conversation with the IRS agent gave me confidence in how to handle my deductions properly. The agent clarified exactly how to allocate expenses when trips had both business and personal components, which was incredibly valuable. For your conference situation, getting official guidance might be worth it rather than guessing.

I have to eat my words about Claimyr. After posting that skeptical comment, I decided to try it because I was desperate to resolve an issue with my missing refund from last year before filing this year's return. I couldn't believe it actually worked - got through to an IRS agent in about 45 minutes when I'd previously wasted entire afternoons on hold. The agent was able to see that my refund had been flagged for additional verification and helped me submit the documentation they needed to release it. She also gave me specific guidance on documenting my home office deduction since I was planning to claim it for the first time this year. Having that direct conversation was way more helpful than reading generic advice online. Sometimes being wrong on the internet isn't so bad!

One approach I've taken that's worked well is the "middle path" on aggressiveness. I claim everything I'm legitimately entitled to with proper documentation, but I'm extra careful with certain deductions that tend to trigger audits. For example, with home office deductions, I'm meticulous about only claiming space used "regularly and exclusively" for business. For meals and entertainment, I keep detailed records of who, what, where, when and why (business purpose). For mixed-use items like your laptop, I use conservative business-use percentages and have documentation to back them up. This approach has served me well for 7+ years of self-employment without audit issues. Being thorough but conservative gives me peace of mind.

Has anyone here been audited before? I'm curious what the experience is actually like for self-employed people claiming home office and business expenses. What did they focus on most? I've heard horror stories but don't know how much is exaggeration.