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

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.

@Cory Gamble do you have their contact number

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.

I would wait a while to get them at a discount but with condos, it always feels like a gamble because of future assessments, fee increases and difficulty getting a tenant approved in a timely manner.

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

Are you willing to gamble your life and those of your family on, "being accountable for your rentals", "being a good landlord", or "maintaining your properties correctly and being decent to your tenants"?

It can still work in niche situations but I think it is a grind and you gamble time and money.