My fiancee and I wanted to buy our first (my second) property out here in Richmond via FHA loan and wanted to house hack as well. We ended up finding a duplex in Highland Park (not a desirable neighborhood, persay) but our tenant pays all of our PITI + $10. The house itself was recently rehabbed and all of the systems were updated. We ended up getting it for $12k below asking. It's a pretty sweet deal, but, like I said, we are living in a C class neighborhood in a C class, 100 year old home. That being said, it has worked out. Our neighbors are all super cool. No break ins. Just don't be a d*** and you should be fine in a c-class neighborhood if you do your homework on crime in the area.
In my novice opinion: If you're looking at student housing in the fan, or museum district, or something like that, you're not going to be cash flowing much if at all. I will say, I'm not sure how capital appreciation is there, but if I recall right, it's not very high.
Church Hill (which I use as a very broad term from Broad St. to Nine Mile,even though it's not Church Hill), except for the far North parts don't even have that good of deals any more either, unless you go to the really run down parts.
It was said before, the deals are out there. One of the best things that I did was paying for a Plus membership to gain access to the investment Calculators. $90 for the year is a steal (as I'm sure the Pro membership is too). Highly recommend upgrading your account if you're serious.
That's my two cents