I know a lot goes into selection of neighborhood, floor plans, schools, etc. but on a more macro scale what measure can be used.

The worst deal I EVER did was with my best friend from High School. 

I have clients that are MD's.How they might want to invest depends on how many years left until retirement.New doctor's just getting into practice have hefty school fees to pay back and also business start up costs with machines etc.

I just default back to what I do were I can open escrow without a contract and with a phone call.. but that's because of the volume of bizz I do with title company .. and our title plants are digital.. so running a title search is not as big an issue like it is in many east coast states I work in.. were they have to actually hire a title abstractor to physically pull title.. ( old school :))

If you are buying property your title insurance company will handle researching the history of the title to the property.  

I've asked the seller for the rental history (has owned 20+ years) and the repair/ maintenance history.

However, I have paid $1000's of dollars to go to Law School and spent countless hours researching the law to know what should not and what SHOULD go into these agreements.

Is it right next to an expensive area with great schools, but still inexpensive?

Issue I'm having is that it is currently owner-occupied so no rental history.  

Some of the wealthiest people in history have said that it's tenacity, resilience, and hard work that make the biggest difference between success and failure in business.