A lot of other markets 20 years from now could be ghost towns with little demand.But on the flipside, that safety/security comes with lessor immediate returns, as is a normal balance with investments (more risk traditionally equals more short term gain potential). 

The court will issue a judgement and that is a form of collection and can allow you to place lien on anything valuable they have.

We always make sure we give them a time frame that leaves some room for errorAlso if we are entering the unit we tell them to not leave any personal any valuables in the open.

Value $900,000; $600,000 debt, $200,000 basis; 7% sales commission, only him- mother is deceased- $250,000 cap gain tax free, $70,000 sales concessions or repairs, capital gain tax on $550,000 less costs,  etc etc.  2 out of 5 year rule, can he live in other buildings?

I would not include appreciation since that is an unrealized gain.

I want to buy him out because the property has a 3% mortgage rate, has gained 100k in equity the last 4 years and cash flows 1k a month.

Equity gained from appreciation is free.  

Thank you so much on the wonderful suggestions and valuable inputs! 

It provided us with valuable insights into STRs as we considered whether this was a real estate investment strategy we wanted to pursue.

They can optimize tax strategies across states and assist with allocating deductions, handling multiple-state filings, structuring future ownership, and advising on capital gains or 1031 exchanges.