You could try the slum-lord route, but dumps, in a dump of a market, focusing on doing absolute bare minimum, dealing with horrible tenants in mass searching for that 1 decent apple in the mountain of rotten ones, hope you survive the costs of such.

Insurance for valuable assets is not like buying a TV - you can't do apples to apples. 

Or should I just be looking to repair the current driveway just to the 2 car area, and leave the tree (was told I could trim roots so it stops growing and lifting the concrete on that side)?

The biggest difference here apples to apples is the one I’m referring to is about 900 square feet bigger and does boast a pretty good view.

Make sure you are comparing apples to apples and be aware that you may be offered a lower rate in year one, only to have it jacked way up in year two.

This is a historic building where two sides require a lift and other sides it is just a ladder.

I believe Apple and Google are expanding their Boulder campuses as well. 

Make sure you understand each GCs SoWs so you are comparing apples to apples.2) Payment and draw schedule - Make sure you understand not only how much it is going to cost, but also when they expect you to pay them.3) Timeline - pretty self explanatory4) Experience and portfolio - Ask them about what kind of construction experience they have and ask to see photos or even in-person tours of past/current job sites.

Quality of life if very good and the city is aggressively working on affordable housing to lift everyone up.

Check out in Apple valley and the surrounding desert areas.