These two elements often get overlooked in the excitement of deal-making, but they play a critical role in the long-term success and sustainability of your investment journey.A well-thought-out tax strategy helps ensure you're maximizing all available deductions, utilizing the most favorable tax structures, and ultimately keeping more of your hard-earned income.

You know the phrase "Don't over improve a property"...this is where your comps are critically important. 

A business model that has always made sense to me is teaching people how to find good deals and have them bring them to me for more critical evaluation and execution where I invest my capital beside yours.

AFFO and DSCR ratios are critical when considering a 721 UPREIT. 

If nothing else, I am sick of paying the quarterly fee to my SD IRA for an asset that might go to zero. do you think you will get bought out realistically .. is the company sitting on cash to allow them to do this ?  

Your points on tenant due diligence and estoppel agreements are especially helpful—understanding existing leases and potential tenant issues seems critical to avoid setbacks.

A lot of my past meetings were cancelled due to Tom supposedly being sick.

Consider a 1031 Exchange:If you sell your Medford rental and reinvest the proceeds into another like-kind investment property, a 1031 exchange can defer capital gains taxes.This is especially attractive if your goal is to scale into higher cash-flow or better-performing markets while preserving your equity.Timing, rules, and proper guidance from a CPA or 1031 specialist are critical to execute this correctly.Other considerations:ADU potential is great for long-term value, but if you can’t fund it now, it’s more of a future option.HELOC or second mortgage: As you noted, rates on rentals are high, so probably not ideal right now.Taxes: Selling your former primary that has never been your current residence won’t give you primary residence capital gains exclusion, but since this was a rental, that may not apply anyway - something to confirm with your CPA.If your priority is financial peace, lowering high-interest debt, and increasing cash reserves, selling the rental and paying down your primary could make the most sense right now.If your priority is long-term cash flow and scaling your portfolio, consider selling and using the capital to acquire small multifamily properties that are cash-flow positive - either outright or through a 1031 exchange to defer taxes.Raising rent is a moderate option if you want to keep the property without selling, but it may only marginally improve your position.Given your flexibility and market knowledge as a realtor, you could likely identify solid small multifamily or even single-family deals that would make option 3 (with or without a 1031) a strong path for long-term wealth.Always happy to share more on what's worked for other investors.

Quote from @Kris Stack: My point is simple—there’s no need for Stuart to publicly criticize those who invested.

It's critical to pick strong materials that will survive long-term tenancy when upgrading a rental home.Just think about what suits you well.