Thanks for the cost breakdown! That's super helpful. Do most of these professionals offer free consultations? I'd like to chat with a few before deciding.

Most reputable tax professionals do offer free initial consultations, usually lasting 15-30 minutes. This gives you a chance to explain your situation and see if they're a good fit, while they can give you a more accurate price estimate based on your specific needs. When you schedule these consultations, come prepared with a list of questions about their experience with multi-state taxation and small business equipment deductions. Also ask about their communication style and availability throughout the year - you want someone who's accessible for questions, not just at tax time. The right professional should feel like a partner in your business, not just a once-a-year service.

I second this! I use FreshBooks for my small business and it makes everything so much cleaner. I upload receipts throughout the year and when tax time comes, I just export everything and send to my EA. She charges me less because the data is already organized.

We usually file ourselves using tax software. Do you think it's worth paying for a CPA just to get help with the IP PIN issue? I'm wondering if the cost would be worth it at this point.

It depends on your situation. If you have a relatively simple return that you're comfortable filing yourself, hiring a CPA just for the IP PIN might be overkill. The services others mentioned like taxr.ai or Claimyr would probably be more cost-effective in that case. However, if you have a more complex tax situation that might benefit from professional review anyway, this could be a good excuse to establish a relationship with a CPA. Many offer reasonable rates for basic returns, and the peace of mind plus PIN assistance might be worth it. Some also offer a free initial consultation where you could ask about their ability to help with the IP PIN specifically.

This is actually bad advice. Filing without your IP PIN when you've been issued one can cause serious problems. The whole point of the IP PIN program is to prevent identity theft, so the IRS will flag your return and it could trigger an audit or further identity verification steps.

This is a great point! I've always found the "don't give the government an interest-free loan" advice to be overblown. With today's savings account rates, the interest you'd earn on that money throughout the year is minimal compared to the stress of potentially owing at tax time. For most W-2 workers, a small refund is actually good peace of mind.

Exactly! I calculated it out and even with a $2,400 refund (which is what I typically get), at 4% interest I'm only "losing" about $50-60 over the course of a year. That's well worth the peace of mind of not having to worry about owing money. Plus, I've gotten much better at immediately putting my refund into my Roth IRA each year so it starts working for me right away rather than getting spent.

Is there an income threshold where this starts to happen? My partner and I both make around $85k and are thinking about getting married next year. Would we be affected by this?

Thanks for this advice! I do have all my trading records going back several years, but they're not organized very well. Do you have any tips on the best way to document the carryover trail? Should I be saving specific forms from each year?

You definitely want to save your full tax return from each year, especially Schedule D and Form 8949. These show your capital gains/losses calculations and carryover amounts. Just as important, keep a separate spreadsheet or document that tracks: 1) Your starting carryover amount each year, 2) How much was used to offset gains that year, 3) How much was used against ordinary income (max $3,000), and 4) The remaining carryover amount that moves to the next year. I also recommend keeping all your original trade confirmations and year-end statements from brokerages. In my audit, the IRS actually wanted to see the original transactions that created the losses in the first place, not just the tax forms showing the carryovers.

That's not accurate. The $3,000 limit ($1,500 if married filing separately) applies to the tax return, not per person. A married couple filing jointly still has the same $3,000 limit as a single filer. The $1,500 limit for married filing separately is because they're essentially splitting the $3,000 limit.

I've never heard of the Voluntary Disclosure Practice before. Is that different from the regular process of just filing late returns? Would I need to do anything special to qualify for that? For records, I have some bank statements showing cash deposits, and I've kept rough notes about my hours and pay rates over the years in various notebooks. Nothing official from the employer though. Would bank statements be enough to show the IRS what I earned?

The Voluntary Disclosure Practice is more formal than just filing late returns. It involves coming forward to the IRS before they discover the non-compliance, providing complete and truthful disclosure, and cooperating with the IRS to determine the correct tax liability. While it doesn't guarantee immunity from prosecution, historically it has significantly reduced the likelihood of criminal charges in cases of willful non-compliance. Your bank statements showing cash deposits will be extremely helpful. Combined with your notes about hours and pay rates, you actually have more documentation than many people in similar situations. The IRS understands that reconstructing income from years ago is difficult, especially with cash payments. They generally accept reasonable reconstructions based on the best available information. Make sure to be consistent and realistic with your income estimates - sudden unexplained variations might raise questions.

This is actually a really good point. I worked as a volunteer tax preparer, and many people don't realize that the EITC can result in substantial refunds for lower-income workers. If your annual income was under about $60,000 (varies by year and filing status), it's definitely worth looking into.