16 Wait seriously? I did some small jobs last year for like $200 each and never got 1099s so I didn't report them. Should I be worried?

12 You shouldn't receive a 1099 until after the tax year ends. Companies are required to send them out by January 31st of the following year. So if you did work in 2024, you won't get your 1099 until January 2025. If you did work in the previous tax year and still haven't received a 1099 by mid-February, you should contact your client. Remember though, even without a 1099, you're still required to report all income you earned.

1 That's actually what I'm planning to do come January when I start my new full-time job, but my concern is about the remaining months of this year where I'm only self-employed. Do you know if there's a minimum threshold of income where quarterly payments become required?

22 The general rule is that you need to make estimated tax payments if you expect to owe $1,000 or more in taxes when you file your return. So if your self-employment income between now and December will result in less than $1,000 in additional tax, you might not need to make quarterly payments. Another consideration is that penalties are calculated based on each quarterly period separately. Since you started self-employment recently, you may only need to worry about the remaining quarters of this year rather than all four periods.

4 I used it last year and found it overestimated what I needed to pay each quarter. I think it doesn't factor in all deductions until you complete your final return. I switched to QuickBooks Self-Employed which gives me more real-time estimates based on my actual expenses and income.

If we go with partnership taxation, do my dad and I need to split everything 50/50 or can we have different percentages? Also, do we need to pay ourselves a salary or can we just take draws?

You can absolutely have different ownership percentages - it doesn't have to be 50/50. Your LLC operating agreement should specify the ownership percentages, and your K-1 forms will reflect those percentages for distributing profits and losses. For a partnership, you don't technically take "salaries" - you take draws, which aren't subject to withholding. However, you'll still pay self-employment taxes on your share of the profits regardless of whether you take draws or leave the money in the business. That's different from S-corps where you'd need to pay yourself a reasonable salary subject to payroll taxes.

For a new LLC filing as a partnership, you'll need to include Form 1065 Schedule B and check the box indicating it's an "initial return." You'll also need to select your tax year (usually calendar year for most small businesses). Make sure you've obtained an EIN before filing - you can't use your SSN for a partnership return.

Does this apply to off-campus apartments too? My daughter lives in an apartment near campus, not in dorms. Can we still count her rent as a qualified expense for her 529 distribution?

Yes, off-campus housing can qualify, but there's an important limitation: the amount can't exceed the room and board allowance included in the school's official cost of attendance figure for federal financial aid purposes. You'll need to contact the financial aid office to get this official figure. As long as your daughter's off-campus rent doesn't exceed that amount, it can count as a qualified education expense for 529 purposes. Just make sure to document everything in case of an audit.

That's interesting and scary. So if the 529 is in my name but my parents are claiming me as a dependent, does that mean NOBODY gets to claim the education expenses paid from the 529? Or do I need to claim the education credits even though I'm a dependent?

The person who claims you as a dependent (your parents) can claim education credits for expenses THEY paid - but not for expenses paid from YOUR 529 plan. The 529 distribution itself isn't taxable if used for qualified expenses, but those same expenses can't then be used to claim education credits. Your parents can still claim education credits for any additional qualified education expenses they paid out of pocket beyond what was covered by the 529 plan. This is why it's so important to keep careful records of who paid what. Many families mistakenly double-dip and claim education credits on expenses that were already paid tax-free from a 529 plan.

This makes a lot of sense. I think I've been expecting mind-reading. Do you have a standard list of questions you ask a CPA before hiring them? I'm wondering if I should be looking for a specialist given my situation with businesses in multiple states.

When interviewing CPAs, I ask about their experience with multi-state taxation specifically, including which states they regularly file returns for. I also ask if they have experience with the specific business structures I use (LLCs, S-Corps, etc.) across different states. I've found that larger regional firms often have better resources for multi-state taxation than solo practitioners, though they can be more expensive. If you have significant business across multiple states, it might be worth the investment. Some CPAs also partner with state-specific experts for jurisdictions they're less familiar with, which can be a good compromise approach.

So what's the solution then? Should small business owners just accept that we're probably missing filing requirements, or do we need to hire one of the Big 4 accounting firms to avoid problems?