If the nonprofit isn't issuing 1099s, they're probably breaking the law themselves. Any business that pays a contractor $600+ in a year is required to file a 1099-NEC. Maybe you should let them know they could get in trouble too? This seems super sketchy for a nonprofit especially.

I'm a tax preparer and I see this situation fairly often. You're absolutely right to report the income regardless of whether you receive a 1099 - that's the law and it's the smart thing to do. Here's what many people don't realize: the IRS has increasingly sophisticated data matching systems. Even without a 1099, they can cross-reference your reported income with things like business expense deductions, lifestyle indicators, and yes, banking activity during audits. They also have agreements with state agencies that might have records of your work. The nonprofit telling you they "have no plans" to file a 1099 is concerning - they're legally required to issue one for payments over $600 to contractors. This could indicate poor record-keeping that might actually make them MORE likely to get audited, not less. My advice: Report the income, keep excellent records of all payments received (bank statements, invoices, contracts), and document any business expenses you can legitimately deduct. If you're audited, having organized records will make the process much smoother. The peace of mind from doing things correctly is worth way more than any short-term tax savings from underreporting.

BE CAREFUL with using Venmo for tax refunds! I've seen numerous issues: • Venmo sometimes flags large government deposits as suspicious • Their customer service is nearly impossible to reach if there's a problem • Some users have had accounts temporarily frozen after receiving tax refunds • Venmo is not a bank and doesn't offer the same protections • If there's an issue with your deposit, resolving it takes much longer than with traditional banks Last year, my refund was held for "review" for 9 days before being released. The IRS confirmed they sent it, but Venmo's fraud department had flagged it. I couldn't reach anyone helpful at Venmo during that time. Never again!

I received my refund through Venmo yesterday (3/14) even though my DDD was 3/15! It posted at 2:18pm EST and showed up as "US TREASURY 310 TAX REF" just like others have mentioned. I was worried about potential delays after reading horror stories, but it actually came a day early. For anyone still waiting, I'd suggest checking your account transcript on the IRS website - if you see the TC846 code with your DDD, the money is definitely on its way. Venmo seems to process these deposits in the afternoon, so don't panic if you don't see it first thing in the morning like with traditional banks. Hang in there!

Has anyone mentioned the impact on their other benefits? When my dad had a big capital gain, it not only increased his Medicare costs but also made him ineligible for some state senior benefit programs for two years. And the extra income pushed his Social Security into a higher tax bracket too.

One strategy worth exploring is a reverse mortgage on their current home. If your parents are 62 or older, they could potentially get a HECM (Home Equity Conversion Mortgage) to access the equity without selling and triggering capital gains. This could provide the funds needed for senior living while allowing them to keep the house for the stepped-up basis benefit. The downsides are that reverse mortgages have fees and interest accumulates over time, reducing the eventual inheritance. But depending on their ages and how long they expect to live, the math might work out better than paying capital gains taxes plus Medicare surcharges. Another angle - if any of you kids were planning to inherit and keep the house anyway, you could potentially buy it from them at a discount (still market rate for tax purposes, but maybe they "gift" you part of their annual exclusion). This doesn't avoid the capital gains entirely but could reduce the taxable amount while keeping the house in the family. Also, definitely double-check the timing. If they can delay the sale until January, that pushes the Medicare premium increases further out. And make sure they've maximized any home improvements that could increase their basis - things like major renovations, accessibility modifications, etc.

Have you looked into cost segregation for your rental property? It's a strategy where you identify parts of the building that can be depreciated over shorter periods (5, 7, or 15 years) instead of the standard 27.5 years for residential rental property. Things like appliances, some fixtures, and even certain components of the HVAC might qualify. This won't get around the passive activity limits, but it can front-load your depreciation deductions, which might be useful when you eventually can use them (either when income decreases or when you sell the property).

This is such a frustrating situation, but you're definitely not alone in dealing with these passive activity loss limitations. I went through something similar last year when I had major repairs on my duplex. One thing that helped me was really digging into the repair vs. improvement classification that others have mentioned. For your situation, the new heat pump is definitely a capital improvement, but depending on how extensive the drywall and carpet replacement was, some of it might qualify as repairs if you're truly restoring to the previous condition rather than upgrading. Also, don't forget that even though you can't use these losses now, they don't disappear - they carry forward indefinitely. When your income drops below the thresholds in future years, or when you eventually sell the property, you can use all those suspended losses. I know it doesn't help your current tax situation, but at least the deductions aren't permanently lost. Have you considered whether you might qualify for the $25,000 active participation allowance? It phases out completely at $150k, but if you're right at that threshold, even a small reduction in AGI through retirement contributions or other deductions might get you back into the range where you can use some of these losses.

One thing nobody has mentioned is that if you gamble at a casino or racetracks, they'll issue you a W-2G for certain winnings (slot jackpots over $1200, etc). The IRS automatically gets these, so you HAVE to report that income. But for sports betting, especially through apps, you might not get any tax forms if you don't hit certain thresholds. Does that mean you don't have to report it? Technically no - all gambling winnings are legally required to be reported regardless of whether you receive a tax form. But realistically...well, you can draw your own conclusions about what people actually do.

This is a frustrating aspect of the tax code that catches many casual gamblers off guard. You're absolutely correct in your understanding - with the standard deduction, you'd report the $120 in winnings as income but couldn't deduct your $120 in losses, effectively creating a tax liability on money you didn't actually profit from. One thing to consider is keeping meticulous records of all your gambling activity, even small amounts. While it won't help with the standard deduction issue, having detailed documentation becomes crucial if you ever scale up your gambling or if your other potential itemized deductions change in future years. Also worth noting that some states have different rules for gambling income and losses, so you might face this issue at both federal and state levels. The math really does work against casual gamblers who take the standard deduction, which is why many tax professionals recommend either going big enough to justify itemizing or staying small enough that the tax impact is minimal.