Don't overlook the potential of utilizing a Backdoor Roth if increasing your W2 wages pushes you beyond the Roth IRA income limits. Anyone can contribute to a Traditional IRA regardless of income, and then convert it to a Roth IRA.

As a fellow S-corp owner who went through this exact optimization process, I'd strongly recommend exploring the defined benefit/cash balance plan route that others have mentioned. You're already doing great with the core strategies, but those additional plans can really move the needle. One thing I learned the hard way: don't just focus on maximizing contributions without considering your long-term cash flow needs. When I first set up my defined benefit plan, I got excited about the huge tax deferrals but didn't fully account for the commitment aspect. These plans require consistent funding for several years, and the IRS gets unhappy if you try to terminate early without good reason. Also, since you mentioned FIRE goals, consider the timing of when you'll need access to these funds. The defined benefit money is generally locked up until 59.5 (with some exceptions), so make sure you have enough in taxable accounts to bridge any early retirement gap. Have you run projections on what your tax situation will look like in retirement? Sometimes it makes sense to balance pre-tax deferrals with some Roth strategies, especially if you expect to be in a similar or higher tax bracket later.

Has anyone here actually e-filed state returns separately? Which tax software actually lets you do this easily? I tried it with H&R Block last year and it was a nightmare - the software kept insisting I file federal and both states together.

I went through this exact situation two years ago when I moved from Wisconsin to Florida mid-year. Here's what I learned from my CPA: You absolutely CAN file your state returns at different times, but there's a critical detail everyone seems to be missing - you need to be very careful about your part-year resident status on each return. For Colorado, you'll file as a part-year resident and only pay Colorado tax on the income you earned while living there (January through July). For Arizona, you'll also file as a part-year resident for the income earned there (August through December). The key is making sure your total income across both state returns matches what you'll report on your federal return. If you're missing Arizona documents, you could estimate based on your pay stubs, but honestly it's safer to wait until you have everything. One more thing - check if Colorado has any special rules about when part-year residents must file. Some states require you to file by the federal deadline regardless of when you moved.

Has anyone tried calling the Taxpayer Advocate Service about these old health insurance penalties? I've heard they sometimes help with IRS issues when you're facing hardship or can't get resolution through normal channels.

I went through something very similar with a 2017 health insurance penalty notice last year. The key thing to understand is that the IRS is definitely still collecting on these, despite what people said back then about being able to ignore them. When I got my CP71H notice, I was also confused about why my refunds hadn't been offset. I learned that the IRS has specific rules about which debts they can offset refunds for, and the health insurance penalty has some restrictions around that process. My advice would be to act quickly on this. The interest keeps accruing daily, and while $711 might not seem like a huge amount, it can grow pretty fast. I ended up calling the IRS (eventually got through after multiple attempts) and they were actually quite reasonable about setting up a payment plan. The agent explained that they're working through a backlog of these penalties systematically, which is why some people are just now getting notices for 2017 tax years. Don't assume this will just go away - the 10-year collection period gives them plenty of time to pursue it. If you can afford to pay it in full, that's probably your best bet. If not, the installment agreement option is definitely worth exploring.

Does the person receiving the house have to worry about property tax reassessment? I know when houses change hands the county often reassesses and raises the property taxes. Would they base it on the $100 sale price or the actual value?

Just wanted to add another important consideration that hasn't been mentioned yet - the impact on your friend's mortgage eligibility if they ever want to refinance or take out a home equity loan later. When lenders do their due diligence, they'll see that your friend "purchased" a $500k house for $100, which creates a massive red flag in their underwriting process. Even if you both properly documented this as a gift transaction with the IRS, mortgage lenders will be extremely suspicious of this transaction history. Your friend might have trouble getting competitive rates or could be denied altogether because lenders will assume there are undisclosed liens, side agreements, or other complications. They may require extensive additional documentation to prove the transaction was legitimate, which could be costly and time-consuming. If you're serious about helping friends buy houses, you might want to consider alternative approaches like providing them with a large gift for the down payment (properly documented) so they can purchase at fair market value, or exploring legitimate seller financing arrangements that don't raise as many red flags with both the IRS and future lenders.

This is a really common issue with rental conversions! One thing that might help is to look at your homeowner's insurance records from over the years. Insurance companies often require you to update your coverage amounts when you make major improvements, so those records can help establish when improvements were made and their approximate value. Also, don't forget about smaller improvements that add up - things like new HVAC systems, water heaters, windows, or even significant landscaping can all be included in your basis. Even if you can't find receipts, you can often get estimates from contractors for similar work done in your area during the same time period. Another tip: if you financed any of the renovations through a home equity loan or cash-out refinance, those loan documents and disbursement records can help establish the timeline and amounts spent on improvements. The key is being reasonable and methodical in your approach - the IRS understands that homeowners don't always keep perfect records, but they do expect you to make a good faith effort to reconstruct the information.

One approach that worked well for me was creating a detailed spreadsheet reconstruction of all improvements made during the years I owned the property as my primary residence. I went through my credit card statements, bank records, and even old photos with timestamps to piece together when improvements were made and approximate costs. For items where I couldn't find exact receipts, I researched what similar materials and labor would have cost during those specific years using resources like RS Means cost data or even old Home Depot/Lowe's catalogs available online. The IRS generally accepts reasonable estimates when supported by this type of research, especially if you can show you made a good faith effort to reconstruct the actual costs. I also reached out to a few contractors I had used over the years - even though I didn't have their original invoices, several were able to provide summary letters confirming the approximate scope and timing of work they performed. This added credibility to my reconstruction. The key is being systematic and conservative in your estimates. Document your methodology clearly so your CPA (and potentially the IRS) can see exactly how you arrived at each number. IRS Publication 551 specifically mentions that taxpayers can use reasonable estimates when records are incomplete, as long as the estimates are based on available evidence and sound reasoning.