Those a little more adventurous might try an “enhanced” buy and hold whereas they take advantage of the following1.

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

Keenan, How's the new adventure going?

I currently work in the Information Technology sector as a programmer analyst and am looking to start this exciting adventure toward financial independence using real estate as the vehicle.  

Skiing in winter, summer outdoor adventure, hiking in the shoulder seasons.

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.

I’m adventurous and travel a LOT!

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

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.