Finally, helping out my friend, hopefully leaving the seller happy with the deal and trading my skills/time for $5k.

Decent cash flow, the dollar stretches a little farther and the rental market is booming!

You have the ability to stretch out that momentum by doing a cash out refinance on the property.

Finally did seller financing for acquisition and spent another 3 months to get the rehab funds from private investors and got it done.

Finally, we get to your original question, of Crystal Clear criteria. 

My advice is to make some offers and use your brother and the due diligence period to make your final decision. 

Only thing you are moat likely referring to is the eviction moratorium finally being lifted. 

I have been following and learning from Bigger Pockets for years. I never had the opportunity to really apply myself to real estate because of the military. About three years ago I decided to retire after 25 years in ...

for example, if land was worth 200k (by county assessor in 2022) but apprasied at 50k at time of purchase in 1988, which number ultimately gets subtracted from the final sale price to calculate the capital gain?

It would kill us if we worked all these years, finally cashed out only to put the proceeds into something that locked our funds up and then handed us back 50% of it.