Do those apps create reports that would satisfy the IRS if I got audited? My spreadsheet has columns for date, client name, property address, and miles, plus notes about the appraisal job.

Yes, the reports from these apps include all the information the IRS requires for documentation. They capture the date, starting point, destination, purpose of the trip, and mileage. Many even include maps of the routes taken which adds another layer of documentation. The IRS wants to see that you're tracking the date, mileage, destination, and business purpose - which these apps record automatically. Some even let you add notes or categorize by client, which sounds similar to what you're already doing manually in your spreadsheet.

I actually went through an audit last year where they questioned my mileage (I'm a visiting nurse). They just wanted to see my log which had dates, patient addresses (no names due to HIPAA), and miles. I had about 22,000 business miles and they didn't question a single entry once they saw my detailed records. Don't be afraid to claim what you're legitimately entitled to!

What kind of attorney should I look for specifically? Is there a certain specialty that deals with trustee misconduct? And roughly what should I expect this to cost? I'm worried about spending a ton on legal fees when the trust assets have already been diminished.

You want an attorney who specializes in trust and estate litigation specifically - not just any estate planning attorney. Many estate planners focus primarily on creating trusts and wills but have limited experience with litigation when things go wrong. Look for terms like "trust litigation," "fiduciary litigation," or "trust disputes" on their website or firm description. Ideally, find someone who has experience specifically with trustee removal cases and financial misconduct. Regarding costs, most trust litigation attorneys work on an hourly basis, typically $300-$500 per hour depending on your location and the attorney's experience. Many states allow for attorney fees to be paid from the trust itself when the litigation benefits the trust (like removing a dishonest trustee), but this usually happens after the case concludes. You might need to pay upfront and seek reimbursement later.

This is an important point. My family went through something similar, and we found that once we filed a police report, the trustee suddenly became much more cooperative with returning funds. The district attorney in our county had a financial crimes unit that took it quite seriously.

Do penalties continue to stack up forever? At what point would they stop adding more penalties?

The failure-to-pay penalty stops when it reaches 25% of the unpaid tax. So if you owe $5,000 in tax, the maximum penalty would be $1,250. However, interest continues indefinitely until the debt is fully paid. One thing I learned through my payment plan is that the IRS applies payments to penalties first, then interest, then the tax principal. This means if you're only making minimum payments, a larger portion goes to penalties and interest rather than reducing your actual tax debt.

I submitted an OIC last year and it got accepted! Settled $27k of tax debt for about $8k. But it's definitely not for everyone - you have to prove genuine financial hardship. They look at your assets, income, expenses... basically everything. And the process took almost 9 months.

This was confusing me too. So if I drive for both Uber and Lyft, that's one Schedule C total? But if I drive for Uber and also do web design, that's two different ones?

Exactly right! Uber and Lyft would be considered the same business type (driving/transportation services), so you'd file one Schedule C combining that income and all related car expenses, phone expenses, etc. But if you drive for Uber and also do web design, those are completely different businesses, so you'd file two separate Schedule Cs - one for the driving income/expenses and another for the web design income/expenses.

This worked for me! I needed to finish ALL the income entry first, then go back to the business section. Thanks for spelling it out so clearly.

That's a really good point I hadn't considered. I make about $65,000 a year, and I've probably lost around $9,000 gambling this year (sadly). Would that raise red flags? Most of those losses were small amounts over many casino visits throughout the year.

That level of losses relative to your income likely wouldn't raise immediate red flags, especially since it's spread out over multiple visits rather than a few large losses. The IRS understands that people don't typically lose their entire gambling budget in one session. Just make sure you've got some supporting evidence beyond just the losing tickets - bank withdrawals at casino ATMs, credit card statements showing charges at gambling establishments, etc. The more documentation you have connecting your financial activity to your claimed gambling losses, the stronger your position would be if questioned. And remember, you're only claiming these losses to offset the winnings you already reported - you're not trying to generate a tax loss beyond that.

Does the player's card tracking actually work for slots too? I mostly play slots and video poker and wasn't sure if those machines track losses accurately.