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 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.

(Cash flow is always a gamble.).

Always run title to check for any clouds, try not to gamble on super small tracts of land like this unless confident in own title searching capabilities.

It's a gamble unless you're experienced and know what you're doing.

Short term "quick money" kinds of opportunities don't really appeal to me as I view it more as gambling.