>If you buy a house, plan around it depreciating.
Unless the country expands or population stops growing there is a limit on the supply of land in the US. It is safe to assume a steady increase in property values over time. Certainly not 90s and early 2000s level, but steady. Even with the recession, housing prices have continued to climb in the US.
Waiting on public transit is definitely a drawback in many places (not in my city), but things like more frequent buses are something we could have if we adjusted priorities as a nation.
You seem to have made good economic decisions (specifically on your car purchase) and should be applauded for that. What I question is a society that explicitly encourages car driving over other forms of transit. This encourages people to make poor economic decisions (ex: car loans, maintenance, depreciation, insurance) because they need a car to survive in our built environment. I do not mean to question your personal decisions.
Rent is usually correlated with density, what do you mean by that?
My car was $1000 used, and in terms of maintenance, the most expensive repair it's needed was $30 (not missing a zero, it's thirty), having the transmission line replaced with a hose because it broke. There have been fluid changes, new tires, DMV registration etc. but that would all be the same in a newer car. I could probably sell it for more than $1000 if I wanted, but I don't want to - 28-38ish MPG and very reliable, a 1998 Ford Escort ZX2.
Haven't recent events in the housing market shown that expecting your real estate to appreciate is a mistake? Real estate can't just keep appreciating faster than inflation forever; greater fool theory only works in a market for so long. If you buy a house, plan around it depreciating.