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?

I also need a general contractor with the same characteristics.

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.

Any attempt to expand or change this market would likely need to address these structural characteristics. 

Don't gamble. 

Its a gamble to go the permit route or not in Philly and absolutely matters the neighborhood/your neighbors as they are usually the folks that will call L&I on you OR if your property is near other construction sites where inspectors would be traveling to/from.