I went through a similar FLP dissolution situation with my family last year. One thing that hasn't been mentioned yet is the importance of checking your state's specific requirements for partnership dissolution. Some states require formal filings with the Secretary of State office to properly terminate the partnership entity, not just the tax aspects. Also, consider the timing of the dissolution carefully. If your parents have significant health issues, you might want to move quickly since the step-up in basis benefit depends on them passing away AFTER the dissolution occurs. If the dissolution happens too close to their passing, the IRS might scrutinize whether it was done primarily for tax avoidance purposes. Another practical tip: make sure your brokerage understands exactly what you're doing. When we dissolved our FLP, the brokerage initially wanted to liquidate everything to cash first, which would have triggered massive capital gains. We had to specifically request "in-kind" distribution of the actual securities to maintain the cost basis benefits everyone's discussing here.

Based on everyone's experiences shared here, it sounds like you're definitely on the right track with your understanding of the step-up in basis benefits from dissolution. One additional consideration I'd add is to make sure you document the business purpose for the dissolution beyond just tax planning. When our family went through this process, our attorney recommended we document legitimate reasons for dissolution - things like simplifying our estate planning, reducing ongoing partnership administrative costs, or giving each family member more direct control over their investment decisions. While tax efficiency is a valid consideration, having additional business justifications helps if the IRS ever questions the dissolution. Also, since you mentioned the partnership agreement doesn't specifically address dissolution scenarios, you might want to review whether it includes any restrictions on dissolution or requires specific notice periods to partners. Some FLP agreements have provisions that could complicate or delay the process, so it's worth checking now rather than discovering issues later when you're trying to move forward. The peace of mind from getting this structured correctly will be worth the upfront planning effort, especially given the substantial unrealized gains you mentioned.

I've been playing social casino games for about three years now and had this exact same worry! I actually contacted a tax professional last year because I was paranoid about it. Here's what I learned: For games like the ones you mentioned (Goldfish Casino, Lucky Time), where you buy coins but can't cash out real money, there's no taxable event. The IRS considers this entertainment spending - you're essentially paying for the experience of playing, just like paying for Netflix or going to a movie. The key distinction is whether you can convert your winnings back to real currency. If the answer is no, then you don't need to worry about tax forms or reporting anything. I've spent over $3,000 across various social casino apps over the past few years and have never received any tax documents, nor should I have. However, definitely keep records of your spending just in case, and be aware that some apps (like Chumba Casino or Global Poker) operate differently - they give you "sweepstakes coins" that CAN be cashed out, and those would be taxable. But for the traditional social casinos you're playing, you're just buying entertainment, not gambling in the traditional tax sense. Hope this helps ease your mind!

I've been dealing with this exact same confusion! I play several social casino apps including some of the same ones you mentioned, and I was really stressed about potential tax implications too. After doing a lot of research and even consulting with a tax professional, here's what I learned: For true social casinos where you can only win more virtual coins (not real money), there's generally no taxable event occurring. The IRS is primarily concerned with actual income - money or prizes that have real-world value that you can cash out or convert. When you purchase coins in these games, you're essentially buying entertainment, similar to purchasing a movie ticket or paying for a streaming service. The virtual coins you win have no monetary value outside the game's ecosystem, so they don't constitute taxable income. However, definitely be aware of these exceptions: - Apps that offer real prizes through tournaments or sweepstakes - "Sweepstakes casinos" where you can convert winnings to actual cash - Any rewards program that gives you real gift cards or merchandise For the traditional social casino apps you're playing, you should be fine. Just keep your purchase records for a few years in case any questions come up, but you shouldn't need to report virtual coin winnings that stay within the game. The key test is always: "Can this be converted to real money or real-world value?" If not, you're in the clear!

Something nobody's mentioned yet - the Augusta Rule has limits beyond just the 14 days. If you're using a home office deduction for the same space, things get complicated. You can't double-dip on deductions for the same space. Also, the business purpose has to be legitimate. Simply calling it a "strategy meeting" won't cut it if you get audited. There needs to be a clear agenda, outcomes, and a business necessity for using the home rather than another location.

I've been following this discussion with great interest since I'm in a similar situation with my consulting LLC. One thing I want to add that hasn't been fully addressed - timing matters a lot for the Augusta Rule. You need to be careful about when you "rent" your home to your business. The rental needs to happen in the same tax year that your business deducts the expense. So if you hold a business meeting in December 2024 but don't actually pay the rental fee until January 2025, you could run into timing issues between the deduction and the income exclusion. Also, for anyone considering this strategy, remember that the 14-day limit is per tax year, not per property. If you own multiple properties and try to use the Augusta Rule on each one, you're still capped at 14 days total across all properties for the tax-free treatment. The documentation requirements everyone mentioned are absolutely critical. I learned this the hard way when my accountant pointed out that simply having meeting notes isn't enough - you need to show that using your home was necessary for the business purpose rather than just convenient.

As a newcomer to this community who's been following this incredibly comprehensive discussion, I wanted to add one more perspective that might help future readers making this decision. Something I haven't seen mentioned is how 401k loans can affect your financial flexibility during economic uncertainty. We've seen how quickly things can change - from layoffs to market volatility to unexpected expenses. When you have a 401k loan, you're essentially committing to fixed payments from your paycheck for years, which reduces your ability to adapt to changing circumstances. I'm also struck by how many hidden complexities everyone has revealed that go far beyond the basic tax question @Anastasia Fedorov originally asked. The job change risks, opportunity costs, psychological factors, market timing considerations - it's clear that "borrowing from yourself" is really borrowing from your future financial flexibility and security. One practical suggestion: before making this decision, maybe try "test driving" the financial impact by setting aside the equivalent of your projected loan payments for 2-3 months while still maintaining your regular 401k contributions. This would help you see if you can realistically handle both the loan payments and continued retirement saving without straining your budget. The collective wisdom shared in this thread shows why communities like this are so valuable - you get insights from real people who've navigated these decisions, not just theoretical advice. Thank you to everyone who shared their experiences and made this such an educational discussion!

As a newcomer to this community, I've been following this incredibly thorough discussion and I'm amazed at the depth of real-world insights everyone has shared! @Anastasia Fedorov, your original question about tax implications has sparked what's essentially a masterclass in 401k loan considerations. Reading through all these experiences, a few key themes really stand out: The **job stability risk** seems to be the biggest concern - that 60-90 day repayment window after leaving employment could create serious tax consequences if you can't immediately repay the balance. @AstroAce and @Diego Vargas's experiences really highlight how quickly this can become a crisis. The **opportunity cost calculation** that @Giovanni Ricci and @Chloe Martin discussed is eye-opening too. It's not just about the interest rate you pay yourself - it's about what that money could have earned staying invested, especially during strong market periods. What really strikes me is how many **hidden complexities** exist beyond the basic "borrowing from yourself" concept. From plan-specific fees that @Ayla Kumar mentioned, to the impact on future borrowing capacity that @Natasha Romanova experienced, to the psychological factors @Anastasia Ivanova raised about changing your relationship with retirement savings. Given your mention of job instability, the collective wisdom here seems to suggest exploring other options first - personal loans, HELOCs, or even @Yara Campbell's suggestion of "test driving" the payment impact before committing. This community's willingness to share real experiences rather than just theoretical advice is incredible. Thank you all for such an educational discussion!

This is a really important topic that hits close to home for a lot of small business owners! I went through this exact same dilemma a couple years ago and almost made the same mistake of skipping the 1099s. Here's the reality: the IRS has automated systems that cross-reference your business expense deductions with issued 1099s. If you claim $5,000 in contractor expenses but don't issue any 1099s, that creates a data mismatch that can trigger an audit flag. The algorithms are getting smarter every year. Beyond the penalties others have mentioned, there's another angle to consider - your contractors might actually need those 1099s for their own tax filing. Some of them might be counting on receiving them to properly report their income, especially if they're working with multiple clients. The paperwork really isn't as bad as it seems once you get organized. I use a simple spreadsheet to track contractor payments throughout the year, and it makes the 1099 process much smoother in January. Just columns for contractor name, address, SSN/EIN, total payments, and whether they hit the $600 threshold. Trust me, the stress of potential IRS penalties and audits is way worse than spending a weekend getting the 1099s done properly. Your future self will thank you for handling this the right way!

I'll add my perspective as someone who learned this lesson the hard way. A few years back, I had a similar mindset - figured I'd just skip the 1099s since I was tracking everything properly in my books anyway. Big mistake! What I didn't realize is that the IRS has gotten really sophisticated with their matching systems. When they see significant contractor expenses on your Schedule C but no corresponding 1099-NEC forms in their system, it creates what they call an "information document matching" discrepancy. This basically puts your return on a list for potential review. I ended up getting a CP2000 notice (basically a soft audit) about 18 months later. Had to provide bank statements, contracts, and invoices to prove all my contractor payments were legitimate business expenses. Even though everything was legal and properly documented, it was still a huge headache and cost me money in accounting fees to respond properly. The worst part? The penalties for not filing the 1099s ended up being more than what it would have cost me to just hire someone to handle the paperwork in the first place. Now I always tell other small business owners - just bite the bullet and file them. It's way less stressful than dealing with IRS notices later. For your international contractor situation, definitely look into the 1042-S requirements. Those have different rules and the penalties can be even steeper if you mess them up.