You'll definitely get the long term appreciation in the San Diego market since our supply levels remain low which helps to insulate our market here, but it will be hard to cash flow on immediately unless you use one of the above strategies I mentioned. 

The college has lots of students, and the surrounding areas have some wealth.

I agree with @Gregory Schwartz that as long as your eyes are open, you are asking good questions, you have resources and have surrounded yourself with a good agent and PM, take the leap and learn as you go.

If the home is 100 yrs old, I'm assuming it's a definite gut which is going to require new plumbing, electrical, heating, cosmetics.I spent about $140K reno on my multi family in the heights on NY ave and there were massive problems with it but it was a gut to 3 units & adding 2 bathrooms, 3 brand new kitchens 4 bathroom reno in total, all new flooring, sheetrock , insulation, framing, doors, electrical, plumbing, paint, parts of roof etc.

Surrounded by the timber industry.   

Are you familiar with the DFW area and surrounding markets?

Our volunteer fire department invites surrounding departments to participate.

I’ve always felt that if I find a property in an area where "I’d want to live," is usually a good sign, but I’m curious how you go about underwriting a deal.I’m in Phoenix, and I’ve been looking at the surrounding cities too.

I make sure they're well insulated, have replacement windows, spend more on nice flooring that looks great (plank style / wood-look porcelain tile, hardwood or click-together LVT planks, not peel-and-stick squares). 

For example, I imagine in a market like Detroit, a neighborhood, at-large, may be filled with mostly Class A properties (in comparison to the rest of the surrounding suburb and/or city); but, I would think that the quality of these properties can be further subdivided within themselves too.