Has anyone here considered just moving to Puerto Rico for the crypto tax benefits instead of these complicated structures? My wife and I are looking at potentially $700k in gains and considering relocating for 183+ days to qualify for Act 60.

I'm in a somewhat similar situation with projected crypto gains around $600K and have been researching this extensively. From what I've learned talking to tax professionals, the CLLC structure can work at our level, but you need to be genuinely committed to the charitable aspect - it's not just a tax avoidance scheme. The IRS looks closely at whether you have a legitimate charitable intent or if you're just trying to dodge taxes. You'll need to demonstrate real charitable giving patterns and have a clear philanthropic mission. The structure works best when you're planning to donate 15-25% of your gains anyway. One thing that surprised me was learning about Charitable Remainder Trusts (CRTs) as an alternative. For your situation, a CRT might actually be simpler and more effective - you get an immediate tax deduction, avoid capital gains on the donated portion, and can still receive income from the trust for years. I'd strongly recommend getting multiple professional opinions before committing to any structure. The setup costs and ongoing complexity need to justify the tax savings, especially since you're dealing with short-term gains which are already taxed at ordinary income rates.

Just to add another perspective - I'm a spouse who didn't file for several years (not quite 12, but about 5). When my husband and I got married, he insisted I get caught up before we filed jointly. I was so embarrassed and kept putting it off, but the mental weight of knowing I was non-compliant was actually worse than the process of fixing it. If your wife is feeling overwhelmed, maybe offer to help her get started with just the most recent year? Breaking it down into smaller steps made it way less intimidating for me. Also, something my husband did that really helped: he didn't judge me or make me feel stupid about it. He just treated it like a practical problem we could solve together. That approach made a huge difference in my willingness to tackle it.

Hey Austin, I completely understand your stress about this situation. You're smart to be thinking about filing separately - that's definitely the safer route given your wife's tax history. One thing I'd add to the great advice already given: even if you file married filing separately this year, you and your wife can still work together to tackle her unfiled returns without it affecting your current tax liability. The IRS treats each spouse's tax obligations separately when you file MFS, so her past issues won't impact your clean record. From a practical standpoint, I'd suggest having an honest conversation with your wife about getting current with her taxes. The anxiety and uncertainty of having unfiled returns hanging over your heads will only get worse with time. Plus, as others mentioned, she might actually be owed refunds for some of those years. If she's willing to start the process, beginning with just the most recent year or two can make it feel less overwhelming. The IRS is generally more interested in getting people back into compliance than punishing them, especially when there's no indication of intentional fraud. Good luck with whatever you decide!

I know this is different from the main QBID discussion, but has anyone had success with the 20% pass-through deduction for rental income when the properties are held in a trust? My family has 5 rental properties in our family trust and I'm trying to figure out if the same rules apply.

The confusion around QBID for rental income is totally understandable - I went through the same thing when I first learned about the 250-hour requirement. What really helped me was realizing that the safe harbor is just ONE path to qualification, not the only path. Here's what I've learned from my own experience with 4 rental properties: even though I don't hit 250 hours, I was still able to claim QBID by demonstrating that my rental activities constitute a legitimate trade or business. The key is showing regular, continuous activity with a profit motive. Some activities that count toward "business-like" operations that many landlords forget to document: - Time spent analyzing local rental markets and adjusting rents - Researching and vetting potential tenants - Regular property inspections (even if brief) - Coordinating with contractors and getting repair quotes - Managing property finances and reviewing performance - Planning capital improvements or property upgrades I started keeping a simple log of these activities, and while I'm nowhere near 250 hours, having documentation of consistent business involvement gave me confidence to claim the deduction. The IRS has been pretty reasonable in recognizing that most small landlords operate legitimate businesses even without massive time commitments. My advice: start documenting everything now, even small tasks. It adds up and paints a picture of genuine business activity.

Another thing to consider is the de minimis safe harbor election which lets u deduct items that cost less than $2,500 per invoice/item instead of depreciating them. So like if ur buying several fixtures and each one is under that amount, u might be able to deduct them immediately even if technically they're "improvements." You make this election every year with ur tax return.

Great question about rental property improvements during vacancy! I went through something similar last year. The key thing to remember is that as long as you're holding the property with the intent to generate rental income, you can start depreciating improvements even during vacant periods. Your timeline looks reasonable - 4 months of improvements followed by finding new tenants shows clear rental intent. However, if your mother-in-law moves in rent-free, that changes everything for 2025. The IRS considers rent-free family use as personal use, not rental use. This means you'd need to stop claiming rental deductions (including depreciation) for the time she's living there. The improvements you made in 2024 during the legitimate vacancy period would still be valid for depreciation, but you'd have to suspend that depreciation during any personal use periods. My advice: keep detailed records of your improvement timeline and costs, and if you do decide to let family live there rent-free, make sure to properly adjust your tax treatment for that period. You might want to consider charging at least fair market rent to keep it as a legitimate rental property for tax purposes.

Another option is to just paper file. Yeah it's slower, but it bypasses all the e-file verification issues completely. Print everything out, sign it, mail it in with your W-2s attached, and you're done. No dealing with AGI verification or PIN issues. That's what I ended up doing when I had a similar issue.

I'm dealing with the exact same issue right now! My husband just got his SSN after using an ITIN for years, and we keep getting rejected for the same reason. Based on what everyone's sharing here, it sounds like there are a few key things to try: 1. Use "0" for prior year AGI instead of the actual amount 2. Make sure to indicate the ID number change somewhere in your tax software 3. Consider getting an IP PIN online if the first two don't work I'm going to try the "0" AGI approach first since that seems to be the most common solution people are mentioning. It's so frustrating that the tax software doesn't explain this ITIN-to-SSN transition issue clearly - seems like it happens to a lot of people! Has anyone found specific instructions in FreeTaxUSA about how to handle this situation? I've been looking through their help section but can't find anything about identifier changes.