One strategy that worked for me was doing partial conversions right after market dips. Since you pay taxes on the value at the time of conversion, converting after values have temporarily dropped means less tax. I managed to convert about $30k of my SEP during market dips last year and saved roughly $2700 in taxes compared to if I'd converted at the peak.

As someone who went through a similar SEP to Roth conversion decision a few years ago, I'd strongly recommend getting a clear picture of your total tax situation before making any moves. At $75k average income with a $68k SEP balance, you have some great options. One thing that really helped me was creating a spreadsheet to model different conversion scenarios. I looked at converting different amounts ($15k, $25k, $40k) and calculated the total tax impact including federal and state taxes. This helped me see exactly where the tax bracket jumps would hit. Since you're self-employed, also consider the timing relative to your quarterly estimated tax payments. If you do a conversion, you'll likely need to increase your Q4 estimated payment or risk underpayment penalties. I learned this the hard way! The flexibility to do partial conversions over multiple years is huge. You don't have to convert everything at once. Many people spread it over 3-5 years to stay in lower tax brackets. Given your income fluctuations as a photographer, you might even time conversions for your lower-income years. Also worth noting - once money is in the Roth, it grows tax-free forever. At 36, you have decades for that growth, which makes the upfront tax hit more worthwhile than it would be for someone closer to retirement.

Don't waste your money on fancy accounting services yet! Your situation is super common. I did the exact same thing with my photography business last year. Just open a spreadsheet and go through your personal account statements. Tag all business expenses and income from the past months. You can absolutely claim business expenses paid from personal funds - the IRS just wants to see that they were legitimate business expenses. For next year, keep it separate from day one. That accounting quote is WAY too high for your revenue level.

Your situation is totally normal for new business owners! I went through the exact same thing when I started my consulting LLC. Here's what I learned: You can absolutely deduct legitimate business expenses paid from your personal account - the IRS doesn't care which account you used, just that the expenses were truly for business purposes. Keep detailed records with dates, amounts, and business justification for each expense. No need to transfer old income to your new business account - that would just complicate your bookkeeping. Start using the business account going forward and treat the past months as a learning experience. That $3,695 quote is absolutely outrageous for your revenue level. I'm doing about $8k monthly and pay my CPA $450 annually for tax prep. For bookkeeping, I use QuickBooks Simple Start ($15/month) and spend maybe 1-2 hours monthly keeping things organized. My advice: create a simple Excel spreadsheet to track your mixed transactions from the past months, then use your new business account religiously going forward. You'll save thousands and actually understand your business finances better by handling the basics yourself initially.

I know several ppl have already mentioned this, but I have to second using claimyr.com to get through. I used it twice this year, once for verification and once for an amended return. Got a live agent both times without sitting on hold all day. Changed my whole tax season experience.

I'm in almost the exact same situation! Filed 2/12, did online verification last Friday, and my transcript is still completely blank too. Reading through all these responses is actually really reassuring - sounds like we just need to be patient for another week or two. The hardest part is not knowing if the verification actually worked, but it seems like most people who completed it online successfully just had to wait it out. Thanks for posting this question, it's helping me stress less about my own situation!

Has anyone considered the actual value of the miles for tax purposes? If you "sell" $1800 worth of flights for $900, are you really making income? Couldn't you argue that you're actually taking a loss on the transaction? I mean, you acquired these miles through spending money somewhere else, right?

I've been dealing with a similar situation and ended up consulting with a tax professional about this exact scenario. Here's what I learned that might help: The key distinction is between the VALUE of what you're providing versus what you're receiving. Even though your brother is getting an $1800 flight for $900, you're still receiving $900 in cash that you didn't have before. From the IRS perspective, that's generally considered income regardless of the "retail value" of what you provided. However, there are a few practical considerations: 1. The airline won't issue you a 1099 for this transaction 2. Your brother isn't a business paying you, so he won't report it either 3. The IRS has limited visibility into these informal transactions That said, technically you should report the $900 as "other income" on your tax return. It's probably only going to result in an extra $200-300 in taxes depending on your bracket, but it keeps you compliant. One alternative approach: instead of a direct "sale," you could book the flight for him as a gift, and he could give you a separate "gift" of money. Gifts between family members under $18,000 aren't taxable to either party. Just make sure the timing and documentation don't make it look like a quid pro quo arrangement.

One thing nobody's mentioned yet - there's a "wash sale rule" that can really mess up your tax loss harvesting strategy. If you sell a stock at a loss and then buy it back within 30 days before or after the sale (61-day window total), you can't claim the loss for tax purposes! I learned this the hard way last year when I sold some TSLA at a loss and then bought it back two weeks later when it dropped more. My tax software flagged it and I couldn't use that $7,400 loss to offset gains.

An additional strategy to consider with losses: if you're in a low income year, you might want to actually harvest some long-term GAINS instead of losses. If your income is low enough to be in the 0% long-term capital gains bracket (under $44,625 for single filers in 2025), you could sell some appreciated long-term investments and effectively pay zero federal tax on those gains. Then maybe save your losses for a higher income year where they'd offset income taxed at higher rates. Just something to think about depending on your situation!