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What type of tenant can you deal with, what type of neighborhood, SF or MF, etc. etc.    

You're right that often the investor may not know what to ask for but more ideally there is someone on the investors side who can collaborate as peers with the contractors.

I recall reading something in The Economist pointing out how these not-so-obvious markets often bring steadiness that flashier spots can’t always match.

they're often much more expensive than they appear because they have deferred maintenance that has been adding up over decades. 

Many nationwide lenders can fund deals regardless of location and often have competitive terms.

It’s older (usually 20-40 years), often don’t have tile roofs or stucco siding and if you ever want to sell, you’re selling to investors as very few are house hacks. 

This is often achieved with written documentation, such as a formal ROW request from TxDOT or other correspondence indicating that condemnation proceedings were possible if no settlement was reached.

I would also keep in mind that very often it is not so much the decision itself but the decision maker that determines the success of a course of action.

A local lender can be helpful since they often understand the market better and may offer more personalized service, but it’s not always necessary if the terms are great.