You have had a wild ride, and I’m glad you shared it with us.  

I don't think many of the new ones will be able to just ride out with the cheapest price strategy.  

On top of that if you don't have wind and hail coverage on your property they probably wont pay at all for a roof replacement.New roofs have can have up to a 25 year warranty if I remember correctly.

People don't seem to mind the short uber ride into downtown

This might rub some people the wrong way. but in my short home buying history, the realtors i have worked with have provided paper work and a way to  get into the house for viewing. other than that i found the house through friends texting me or riding around or Zillow. 

Real estate on leverage has worked for people every time except GFC, if this happens within next 5 years then can be in trouble, but make sure you can ride a huge downturn.  

The "Youtube" culture of gurus were able to really ride the wave of what was 2010's where you could get lucky pretty easily.

In our 15 min ride to get tacos, with 2 others guys my age, he asked what type of retirement plan each of our employers gave.

Whether they are there for the lake or riding the bike trail. 

Subject To, improperly taught, is like riding a Unicycle down a steep hill with no brakes.