I'm about ready to retire so I'm not looking to compete in a bidding war, mainly looking for a fair deal that I can rehab or a turnkey with some cash flow. 

Airbnb algorithm is a mystery somewhat - but the algo does factor your cleaning fee, cancellation policy, review score, and more when factoring visibility.

The main issue is land... or lack-there-of.

It's my understanding that the city is responsible for all the piping up to the curb stop in my front yard and I am responsible for the curb stop to my property.Yes from the water meter to the house is generally the owner and from the main line to the meter is generally the city.. 

Cash flow is mainly a mechanism of leverage in the deal.

You have a good point about the hassle factor though. 

Most of our investments we look at IRR (time value of money) to determine which investment is a good fit for us at this time - which factors in returns, risk and time of investment - is it a short term investment we want to get appreciation play or long term fixed income investment.

We mainly own SFR and do LTR but last year we added our first STR and its been a great experience.

The main property will be my primary residence.My biggest question is, what kind of foundation would you use, (that is to code and will pass inspection/permits in Charlottesville) that is either relatively easy DIY or cheap to outsource.

I made the layout more user friendly, added a whole wall of closets in the main bedroom, totally gutted kitchen and bath.