If you are looking at 75 to 100 year old property, you will be smack dab in the middle of Knob and Tube, Lead paint and asbestos eras. If they have been reno’ed, make sure permits were pulled and signed off on. Better make sure your ‘Whoopsie’ fund is large and paid up, anything from that era should be on it’s third set of windows.
Avoid HOA’s and Condos like the black death.
Make sure there is a buttload of insulation in the attic. Second to that, make sure the attic is ventilated.
Watch a season or two of 'Holmes Inspection’
Figure out where the nearest HD or Lowes is. It will become your second home 
Definitely talk to the neighbors. When we bought our house, the neighbor told us that there’s an adult group home up the street (sort of an assisted-living situation). It wasn’t a deal-breaker, but it was good info to have. Neighbors will tell you all kinds of stuff about the neighborhood that you probably won’t find out from the sellers or your agent.
Regarding school districts, my personal advice – I know some may disagree – is to worry more about the overall quality of the district, instead of individual schools. For one thing, zoning can change so that you’re no longer at the same elementary school you were previously. For another, principals and teachers can switch in and out. But if the district is good, most of the schools in it will usually be good, so it won’t matter as much if you get “the” school. That’s been our experience, anyway.
There’s some really great advice in this thread. Particularly about checking for drainage, and making sure you’re not where the school bus stops.