If it was a middle of no-where or rural area and the the city is expanding, its practically a gamble on when the price would be right since there market will be providing newer and normally better houses.

I live in S Fla so unless you gamble, just want management fees or are happy to park money... buying MF is not really happening ... right now it’s about waiting for nervous developers to capitulate in bulk or making deals with the loan to own lenders last in the door 

If one has to take care of other family members, then that adds another level of stress and complexity.If someone is on their own and wants to gamble, sure, some will take a shot.

Aside from that, it is an immersion. 

If any of you reading this are from the Rhode Island area and would like to connect, please reach out as I'm trying my hardest to immerse myself into this community and Real Estate at large!

Thank you.It does vary quite a bit from street to street, but no matter how you slice it, it's a gamble in that area.

If you could BRRRR and time the interest rates well Otherwise, Buying a property that is negative cash flow without any forced appreciation or a clear short term upside(flip) might be described more as gambling then investing.  

but in my view it makes a relatively "safe" investment in cash flowing real estate into a gamble on appreciation.    

One learns very quickly and unfortunately usually the hard way that cash tenants are a huge gamble and that section 8 is the only way to find healthy, consistent, positive cash flow in Detroit and many of the other inner cities accross America.

I hear what you're saying about the cost to make them habitable but I don't think that will be considered a gamble when you're looking backwards a few years from now.