Other investors gambled, overpaid, negatively cash flowed, and got wiped out.

Plenty of times I have received fraudulent applications. https://www.biggerpockets.com/forums/52/topics/82174-ultimate-guide-to-tenant-screening-and-renting-your-house

Real estate is a big lumbering elephant compared to the nimble stock market, but it's still a gamble to wait to time the market for downturns and upturns.   

When I initially called Arlington Police I was given the District Attorney's office phone number to report fraudulent business practices based on irresponsibly renting to people without checking on them at least a little; No managing and knowing who lived there besides the name of the tenant'  It appears others lived there.

Buying a home with the idea of selling it (at a profit) is more of a gamble than a strategy unless you buy something with the intention of doing a live-in flip.

Yes our research says that it would be a gamble and not  much cash flow if any at the1500s.

And what kind of gamble are we investors making, when most MF loans are only locked in for 5-7 years?

@Andrew Easterling  Roxbury is historically one of the worst areas of Boston for crime - but it's gentrifying as other parts of Boston are priced out of sight.For example, duplexes in Boston as a whole range in price from $589,000 (Mattapan) to $4.65M (Back Bay).If you want to gamble on a high crime area in the path of gentrification, I'd consider Mattapan. 

It is always a gamble when buying a condo unless maybe it just received its recertification recently.

Smart investors make their money when they buy - waiting for appreciation seems to be a bit like gambling.