May just have to be patient and wait for the delinquency issue to get cleared up so as to get the FHA approval back so I can sell the 4 units I can't rent or possibly go the owner financing route which I'm not thrilled about.

That appraisal fee was a gamble, and it doesn't always pan out.

If you need a concealed carry permit and a Kevlar vest, then unless you are some sort of Property Manager Warrior with a thrill for adventure, then you will lose 95% of the time.  

Probably a bit of a gamble to waive some of my rights, but really wanted to push this deal thru

The stock market and rates are a gamble and if I were your bank looking to finance you more property I would take that into consideration for your business plan.

@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. 

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.

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

It's a gamble, but an exciting one.

I say if your worried about it don't take the gamble.