Just my thoughts:
If you like new houses/interiors/amenities, buy a new(er) house. I bought a house built in the 90s and regret all the upgrades I am currently having to do.
Without kids 1400-2000 sq feet seems to be enough room. Now with 2 kids I am looking to upgrade to 2000+ sq feet within a year or 2. Going to look at new builds.
Patio > Deck
3 car garage for my next house is a must + room for a potential additional detached garage.
Watch out for anything built near property lines. It could be a problem down the line. Even auditor maps can be a bit off.
Negotiate your ass off. The people we bought from wanted to take all the appliances, etc. Make sure you get all the crap when buying the house + whatever other extras you can manage.