Are you aiming for part time / passive investment or full time immersion?  

@Ashley Gamble not sure how I didn't see this before but I hope you have made progress on this issue by now.

They didn't want men gambling away the house in a poker game and leaving the women and children without a place to live.The intent I think for a home to be designated your homestead is that is where you live. 

If you invested $50k or $100k would that $10k or $20k be better investing it in a lower risk asset or continue to take the gamble of red vs black?

Guys with problems end up gambling everything away because they've lost too much to walk away now.

Holding onto a property merely for tax considerations is a dangerous gamble.But if you want to gamble - yes, selling in a year without a W2 job usually saves on taxes.

I know that sounds crazy, and you and I would never think to do it, but people do.At the end of the day, inheriting tenants is a gamble and risk you need to factor in.

The area does not have explicit rules on STRs so its a gamble with that strategy.

Don't gamble. 

Focusing just on appreciation causes people to take on negative cashflow situations, gambling that the market will eventually save them before they run out of cash.