Thank you for this suggestion. I did actually meet with HR yesterday and showed them that I've started the process. They were more understanding than my direct manager and said they mainly need to see proof that I've engaged with a tax professional and have a concrete plan. Did you use a special type of tax person for your situation? I'm wondering if I need someone who specializes in delinquent returns.

I used an Enrolled Agent who specialized in tax resolution and delinquent returns. They tend to be more affordable than CPAs while still having full representation rights with the IRS. The key is finding someone who regularly handles past-due filings rather than just normal tax prep. I recommend asking specifically about their experience with employment verification issues and their typical timeline for preparing delinquent returns. My EA was able to provide a formal letter stating I had retained their services and outlining our filing plan, which satisfied my employer while we completed the actual work. Most tax pros who work in this area understand the employment implications and can help document your progress for HR.

This is so important! I had the same issue with state taxes being overlooked. And if you had self-employment income, some cities and local jurisdictions also require tax filings. For example, I had to file a city income tax return for my freelance work that I didn't even know existed until I got a notice.

How much did TaxAct charge for each prior year? And did you have any issues with the 2017 filing from the accountant?

TaxAct charged around $60-70 per year for their business editions when I used them, though prices may have changed. I found it reasonable considering the alternatives. For the 2017 return, the accountant charged me $350, which was actually less than I expected. There weren't any issues with the filing itself, but they discovered I had been calculating depreciation incorrectly on some equipment, which affected the subsequent years. This meant I had to make some adjustments to my 2018-2020 returns as well. If you have depreciating assets, make sure you're tracking them consistently across all tax years - that's something the software won't necessarily flag for you.

UltraTax is professional-grade software used mostly by accounting firms, not really meant for individuals. For DIY, stick with TaxAct, TaxSlayer or H&R Block's prior year versions as others suggested. Much more user-friendly and way cheaper.

7 Does VITA actually help with learning business tax prep though? I thought they only do basic 1040s and don't handle Schedule C filers?

20 You're right that VITA primarily focuses on basic returns, though some sites do handle simple Schedule C returns with limitations on income amounts and deductions. It won't give you comprehensive business tax experience, but it does provide excellent training in the fundamentals and client interaction skills. For business tax experience specifically, you might consider trying to work part-time at a local CPA firm during tax season. Many firms hire seasonal preparers and will train you on their procedures. Another option is finding a mentor through your local chapter of the National Association of Tax Professionals (NATP) or the Texas Society of Enrolled Agents.

13 I started out charging by form and it was a DISASTER. Clients hated the uncertainty and I had to have awkward conversations when additional forms were needed. Now I do tiered flat fees based on return complexity (basic W-2 only, itemized deductions, Schedule C, etc) and both me and my clients are much happier.

Can you explain more about the mega backdoor Roth through an S corp? My accountant mentioned this but didn't explain how it actually works with the S corp structure specifically.

Sure thing. The key is setting up your Solo 401k plan with the right provisions. Your plan needs to specifically allow for both after-tax contributions (beyond the normal $22,500 employee limit) and in-plan Roth conversions. With an S corp, you wear two hats - employee and employer. As employee, you contribute up to the standard limit ($22,500 for 2023, plus catch-up if over 50). As employer, your S corp can contribute up to 25% of your W-2 wages. Then, if your plan allows it, you can make additional after-tax contributions up to the total annual limit ($66,000 for 2023 combining all sources), then immediately convert those after-tax dollars to Roth. This gives you way more Roth conversion potential than just the standard backdoor Roth IRA.

Does your S corp pay for these directly, or do you pay personally and get reimbursed? I've heard conflicting advice on the best approach.

Thanks for mentioning the state reporting requirements - I hadn't considered that. Do you recommend any particular approach for the catch-up adjustment if we find the depletion has been incorrect in prior years?

For catch-up adjustments, I typically use a cumulative approach rather than amending prior returns. Calculate what the correct cumulative depletion should have been through the current year based on actual harvests using the corrected depletion rates. Then adjust the current year depletion to reach that cumulative total. Include a disclosure statement explaining the methodology and calculations. As long as you're not changing the total basis, just reallocating between timber types, this approach has been accepted in my experience. The key is thorough documentation of volumes, rates, and calculations to show the trail from old to new reporting.

I've used TimberTax Pro for the last 3 years and it's been worth every penny for our timber clients. It handles the Form T complexity much better than regular tax software, especially for tracking multiple timber accounts and different measurement units.

Thanks for the recommendation! I'll look into TimberTax Pro. Does it integrate with any of the mainstream tax preparation packages or is it standalone?