I hadn't considered bankruptcy yet. That feels like a last resort to me, especially since I'm trying to restart my business. Would the 2021 crypto tax debt even qualify since it's more recent? And wouldn't bankruptcy make it impossible to get business loans or credit in the future?

You're right to be cautious about bankruptcy. The 2021 crypto debt wouldn't qualify yet - tax debts must generally be from returns due at least 3 years before filing bankruptcy. So that major portion of your debt wouldn't be dischargeable right now. Bankruptcy does seriously impact your credit and ability to get business financing - typically stays on your credit report for 7-10 years. Since you're restarting your business, this could definitely create significant obstacles. Many business loans, commercial leases, and vendor credit arrangements check bankruptcy history specifically. I'd exhaust all options with penalty abatement and payment plans first before considering this route.

This is really important advice! I made a partial payment on my tax debt without understanding the implications and it reset the 10-year collection statute. Definitely talk to your LITC advisor first.

This is interesting! How much does this arrangement cost you annually, if you don't mind sharing? I'm trying to budget for these services but have no idea what's reasonable.

I pay my CPA about $3,500 annually for tax planning and preparation, including quarterly check-ins. The estate attorney was more of a one-time expense (about $5,000 to set everything up), with smaller fees for updates ($500-1,000 when needed). The bookkeeper costs me around $300/month to handle all the rental property accounting and documentation. So all in, it's roughly $12-15K per year, which seems like a lot but has actually saved me more than that in tax efficiency and better property management. Plus the peace of mind is worth a lot - I was making costly mistakes trying to handle everything myself.

What specific questions would you recommend asking? I always feel so unprepared when interviewing financial professionals and end up just nodding along to whatever they say lol

I'd ask scenario-based questions rather than general ones. For example: "If I wanted to transfer rental property to my children's trusts, how would you approach that to minimize tax implications?" or "How would you handle depreciation recapture if I wanted to sell one of my properties and use a 1031 exchange?" Watch how they explain complex concepts - a good accountant will make things clear without talking down to you. Also ask about their communication throughout the year - will they proactively contact you about tax law changes that affect your situation or just see you at tax time?

Did the conversion process mess up your ability to take the QBI deduction that year? I heard entity changes can disrupt that 20% pass-through benefit.

The conversion actually didn't disrupt my QBI deduction that year. Since I went from one pass-through entity (Nevada LLC) to another pass-through entity (Wyoming LLC), the basic eligibility wasn't affected. However, I did have to carefully document the transition date and maintain separate accounting for the pre and post-conversion periods. The tricky part was that the conversion created a "short year" for tax purposes, which required some additional form filing and proration of certain expenses. I recommend getting a tax pro involved if you're considering a similar move.

Yeah, the Corporate Transparency Act is hitting every state. Started in January 2024. Every LLC, corp, etc has to report ownership to FinCEN. Doesn't matter which state anymore - Wyoming, Delaware, wherever - the privacy benefit is mostly gone now.

Thanks for confirming. That's disappointing since privacy was one of my main reasons for choosing Wyoming. Guess I'll focus more on the tax benefits now since that privacy advantage is diminished.

Oh wow I had no idea about quarterly taxes. How do you know if you need to pay them? And what happens if you haven't been paying them all year?

Generally, you need to pay quarterly taxes if you expect to owe $1,000 or more when you file your return. It's basically a pay-as-you-go system for income that doesn't have taxes automatically withheld like your W2 jobs do. If you haven't been paying them, you might face an underpayment penalty when you file. The good news is that if this is your first year with 1099 income, you might qualify for a waiver of the penalty. Moving forward, you'll want to make estimated payments every quarter (April 15, June 15, September 15, and January 15) based on what you expect to earn.

You can offset some of this though! You can deduct business expenses against your 1099 income, which lowers your taxable income. Things like software subscriptions, equipment, home office, internet, phone, professional development, etc. can all potentially be deductible if you use them for your freelance work.

Thanks for this info! My fiancée and I weren't planning to get married until after graduation, but maybe we should reconsider the timeline if it would help with financial aid. Would getting married now affect her financial aid situation too? She's currently classified as a dependent student on her parents' taxes.

Getting married would make both of you independent students for FAFSA purposes, regardless of whether your parents still claim either of you as dependents on their taxes (those are separate systems). This could be beneficial for both of you if your incomes are lower than your parents', as financial aid would be calculated based only on your finances, not your parents'. However, it could potentially reduce aid if one of you has significant income or assets that would now be counted toward both of your FAFSAs. Marriage also makes you eligible to file taxes jointly, which could have its own implications.

This is smart advice. I did the community college route too for similar reasons. Saved a ton of money and still got my teaching degree. Many community colleges also have special institutional scholarships that don't require FAFSA completion.