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.

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.

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. 

I’m not sure how to judge all those characteristics you mentioned before but I’ve been feeling pretty confident about the mortgage agent and their work.

I have a nearly perfect credit score and I'm gambling on that for my first project.

Overall I would treat this investment as a high risk gamble and willing to accept loss if it failed but It's also a very interesting process to understand how the industry works.