Well-maintained sidewalks not only improve the aesthetics of the property, but they also protect inhabitants' safety and convenience.

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

They're incentivized to make/save as much as possible from the deal so I wouldn't be surprised if they aimed to cut costs in a situation like this. 

An owner will sell off market for convenience some times, but it is mostly because there is a problem that needs to be solved prior to it being market ready that they cannot afford to or do not know how to solve. 

You may know this already, but out-of-state investors are also sometimes surprised by Texas’ “high” property tax rate (but no personal income tax).  

To my surprise, the owner is also a local councilman and recently faced many lawsuit charges.

So the buyer is really finding the house anyway, they'll likely find FSBO (unless you have a crap realtor that filters those out, which wouldn't surprise me). 

It needs to be in a convenient location with rising value.

Not saying this is the case... but with proper tax planning there should be zero surprises.

I personally don't like being bound by the restrictions of an old home - discovering all sorts of surprises behind the walls.