However, I wouldn't necessarily recommend full replacements of any or all of them. 

Unfortunately - my current lot for my primary is 1 acre and VERY sloped, and close to a water source (creek), so the county has not even allowed me to permit my downstairs finished basement without an extremely costly renovation to our septic (over $60,000, and that doesn't count demo'ing and replacing our driveway to get to the existing tank and leachfield), and even if I could permit it, it would essentially need to be a treehouse in the redwoods due to the slope (not a bad idea though, I would actually love a livable treehouse on this lot!

He's in an age and stage of life where he needs cash, not investments.He is fine with me replacing the tenant at market rate if that's what I need to do.

@Dallas Smith To defer capital gains on your investment property, a 1031 exchange is an effective strategy, but the replacement property must be held for investment purposes for at least two years.

Only thing I could think of is to institute a large sales tax to replace it.

I gave her 30k in 2024 and that was to buy a new car to replace her 15 year old Accord (which just keeps on running). 

Financial freedom isn't simply about replacing your current income, because inflation continuously drives up prices, making a fixed income insufficient to maintain your standard of living.

If you're insuring a home to replacement cost, insurance companies don't care about appraisals or what the home is worth.  

in other words, if the roof blows off a FedEx building, do they typically get a loan to replace it, or are the investors assessed? 

If it all checks out OK, they could just replace that section, mud, tape and paint and it'll only cost you a few hundred bucks rather than filing a claim with your insurance.