1 Thanks for mentioning this! I completely forgot about the worksheet that comes with the form. Is it really accurate though? I've heard mixed things.

11 I've found it to be surprisingly accurate for straightforward situations. I have two W-2 jobs with similar pay levels and following the worksheet got me within $200 of breaking even last year. Where it gets less reliable is if you have more complex situations like self-employment income, substantial investment earnings, or major deductions outside the standard deduction. In those cases, the IRS Tax Withholding Estimator or one of the other tools mentioned here would probably work better.

19 This is great advice! I used to try to get it exactly right but would stress when I ended up owing even $100. Now I just aim for a small refund too and it's much less stressful.

Thanks for this advice! I didn't know about the Taxpayer Assistance Center option. Do I need to bring anything specific to the appointment? And will they be able to tell me if my return was received even if it's not showing up in their system yet?

Bring a copy of your tax return, your certified mail receipt, photo ID, and any other correspondence you've had with the IRS. These in-person representatives can access different systems than the phone reps sometimes can, so they might be able to locate your return in a different status or location. They can also initiate a formal trace on your return using your certified mail information, which is much more effective than trying to do it over the phone. If they can't find it, they can help you submit a replacement return properly marked so it doesn't create issues. The in-person help is seriously underutilized but much more effective.

That's actually a smart idea. What fax number did you use? I didn't even know the IRS accepted faxes for tax returns.

Would doing it that way cause any problems with e-filing? I'd really prefer not to mail in a paper return if possible. Does OLT allow you to attach explanatory statements to e-filed returns?

You're right to be concerned about e-filing. Most software doesn't allow attaching explanatory statements to e-filed returns in the same way you can with paper returns. Your best option with OLT would be to use their "Additional Information" or "Miscellaneous Notes" section if they have one. Enter a detailed explanation there about your HSA contribution calculation, specifically mentioning the catch-up amounts and why they're correct. This gets transmitted with your e-filed return. If OLT doesn't provide that option, you might need to either paper file or use different software that handles HSA catch-up contributions correctly.

This actually worked for me with FreeTaxUSA! I had a similar HSA calculation issue and redistributing the contributions fixed it. Just make sure the actual contributions match what you're reporting - you might need to make adjustments with your HSA provider if the real-world contributions were different.

16 Do you have a recommendation for tracking mileage? I sometimes drive to client sites and I'm terrible at remembering to log it.

7 I use MileIQ for tracking mileage - it runs in the background on your phone and automatically detects drives. You just swipe left for personal trips and right for business trips. Super easy and creates IRS-compliant records. For quarterly taxes, I set aside 30% of every payment I receive into a separate savings account. That usually covers both federal and state taxes, plus the self-employment tax. Then I make payments online through the IRS Direct Pay system every quarter.

11 This is great advice! Does the Solo 401k have the same contribution limits as a regular 401k? And can I still contribute to my Roth IRA too?

Ooh, that's interesting about self-rentals. What about if I own a single-member LLC that owns both my business and a building, and the business operates in that building? Would that qualify as self-rental for QBI purposes?

For self-rentals and QBI, the key is having common ownership between the rental activity and the operating business, not necessarily the exact same entity. If your single-member LLC owns both the business operations and the building, it's actually simpler - it's all within one entity so there's no "rental" happening for tax purposes. The self-rental rule typically applies when you have separate entities or activities - like if you personally owned the building and rented it to your LLC business. In that case, the rental income would generally qualify for QBI regardless of whether the rental itself meets the trade or business standard.

Triple net leases are specifically mentioned in IRS guidance as potentially problematic for QBI. In Rev. Proc. 2019-38, they explicitly excluded triple net leases from the safe harbor. But that doesn't automatically disqualify you from claiming QBI - it just means you can't use the safe harbor provision.

Thanks for clarifying that! So I'd need to prove my triple net lease activities constitute a trade/business outside of the safe harbor? Sounds like an uphill battle given how passive those arrangements are by design. I might need to talk to my accountant about this one.