Has anyone else successfully charged between their own business entities like OP is considering? I'm in a somewhat similar situation with a consulting business and a rental property, and I sometimes do consulting work that benefits the rental. Never thought about actually charging between them.

This is a really nuanced situation that requires careful handling. Based on what you've described, you're actually in a decent position to maintain business classification despite the recent losses. For your first question about the vacation rental paying your advertising business - this is absolutely legitimate as long as you treat it like any other business transaction. Create proper invoices, document the services provided, and charge fair market rates. This can actually help your Schedule C business show some income while providing a legitimate deduction for your rental property. Regarding the hobby classification concern - don't artificially inflate profits by not reporting expenses. Instead, focus on documenting your profit motive. Since you've had profits for most of the 20 years, that's strong evidence in your favor. Make sure you're documenting: - Your business plans and efforts to return to profitability - Marketing activities to drum up new clients - Any changes you've made to improve operations - Your expertise and time invested in the businesses The IRS looks at the totality of circumstances, not just recent losses. Your long history of profitability combined with documented efforts to improve the struggling business should support your business classification. The fact that you're actively trying to get new clients for the low-revenue business is particularly important to document. Consider keeping detailed records of your business development activities, client outreach efforts, and any strategic changes you're implementing. This demonstrates the businesslike manner and profit motive the IRS looks for.

Has anyone dealt with a situation where they rented out part of their house during the ownership period? I'm in a similar situation as OP but I rented out my basement for about 4 years of the 15 I've owned my house. Not sure how that affects the capital gains exclusion.

Just wanted to add another important consideration for your situation with your son on the deed - make sure you understand the "lookback" rule if you're planning to sell in 2026. If your son was added to the deed for estate planning purposes but hasn't met the 2-year ownership requirement yet, you might want to time the sale strategically. For example, if he was added to the deed in early 2024, he'd meet the ownership test in early 2026. Combined with the use test (if he's been living there), this could make a significant difference in your tax liability. Also, since you mentioned you've lived there 18 years continuously, you definitely meet both tests for the full exclusion. Just make sure to keep good records of when your son was added to the deed and his residency status to properly calculate each person's eligibility when you file.

Pro tip: Start using your player's card! It's literally the easiest way to track your gambling. I resisted for years because I thought casinos would somehow use it against me, but now I always use it. At the end of the year, every casino will provide you with an annual win/loss statement if you used your card. It's official documentation that the IRS respects way more than personal notes. Most casinos let you request it online now.

One thing I learned the hard way is that you absolutely need to keep receipts for any cash you withdraw at the casino ATMs. Even if you don't use a player's card, those ATM receipts help establish a paper trail that shows you were actually gambling the amounts you're claiming as losses. Also, if you're serious about deducting gambling losses, consider opening a separate bank account just for your gambling activities. Transfer your gambling budget to that account, and only use that debit card at casinos. This creates a clear financial trail that's much easier to track and defend if the IRS ever questions your losses. The key is being able to show that the money you withdrew actually went to gambling, not other expenses. Having dedicated gambling funds makes this much clearer than trying to sort through your regular checking account transactions.

I've been a retirement plan administrator for years and see this confusion all the time. When a 403(b) has both pre-tax and after-tax contributions, the rollover reporting can get messy. The distribution code "BG" is telling you something important. The "B" means qualified plan distribution, and the "G" specifically indicates this includes after-tax contributions. Those after-tax contributions ($12k in your case) should roll into your Roth IRA tax-free since you already paid tax on them. Only the earnings on those after-tax contributions (the $2k difference) would potentially be taxable when moving to a Roth. But if this was a direct transfer between trustees, even that might be reported differently. The blank in box 2a with unchecked box 2b is basically the provider saying "we don't know your tax situation, so we're not specifying the taxable amount.

Has anyone used TurboTax to handle this kind of situation? I'm going through something similar and wondering if the software can handle these complex rollover situations correctly.

I just went through this exact same situation with my Empower rollover! The BG code combination was throwing me off too, but after speaking with a tax professional, here's what I learned: The "B" indicates it's from a designated Roth account (like Roth 401k), and the "G" confirms it was a direct rollover. Since you rolled from one qualified plan to another, this should be completely non-taxable. The blank box 2a with "Taxable amount not determined" checked is actually normal for these situations. Empower is basically saying "we're not calculating the taxable portion because this should be handled as a rollover by the taxpayer." When I entered mine in TurboTax, I just had to make sure to answer "Yes" when it asked if this was a rollover. The software automatically treated it as non-taxable after that. You definitely still need to report the 1099-R on your return though - the IRS needs to see that you received it and properly handled it as a rollover. The different amounts in box 1 vs box 5 just represent your total distribution vs your original contributions. Since it was a proper rollover, you don't need to calculate anything - just report it correctly as a rollover and you should be all set!

I had a very similar situation last year with my 401k rollover and those BG codes on the 1099-R form. What helped me was understanding that you absolutely need to report this on your tax return even though it's not taxable - the IRS cross-references the 1099-R they received from Empower with what you report. The key thing is when your tax software asks about the distribution, make sure you clearly indicate it was a "direct rollover" or "trustee-to-trustee transfer." Most tax software will have a specific question about this. Once you mark it as a rollover, the software should automatically treat the entire amount as non-taxable. One thing to double-check: make sure the rollover was completed within 60 days if it wasn't a direct trustee-to-trustee transfer. If it was done properly between the two Empower accounts, you should be fine. The blank box 2a is actually working in your favor here - it means Empower isn't claiming any portion is taxable, which is correct for a proper rollover. Don't stress too much about calculating the taxable portion yourself - that's exactly why they left box 2a blank and checked the "not determined" box. Just report it accurately as a rollover and you'll be good to go!