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.

When I asked him about asset protection and trusts he was pretty clear that unless I owned a good amount of properties it wouldn’t make sense for me to open trusts or set up offshores.

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. 

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.

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.

@Cory Gamble do you have their contact number

Thats not a wise gamble in most cases if there is a market change for any unknown range of factors.