Ok, so generally, barring world-changing events, stuff.. fluctuates, yes, but when it reaches a certain point, something pulls it back towards the average.
If house prices go up, wages go up, inflation goes up. If property tax goes up it might lead to more people renting rather than owning, hence higher rents in the long run.
I guess I'm saying.. there are micro and macro factors. And, it's impossible to see the future. If a house cashflows well now, and there aren't massive black clouds on the horizon, it's probably an ok bet. Don't over-extend yourself, make sure you have contingency so you don't lose the lot.
High property tax is, to me, a significant risk as you must carry that in a bad situation. You can *try* to pass on prop tax rises but the truth is really you'll be charging what the market thinks you should charge - if there is a mass exodus from Chicago, you're forked, either way ;)
Detroit.. yeah, special. Inflation and rising bond prices will, I believe, help the other pension funds out (until next time...).
As to the post title - if that's how you feel, RUN away. You won't sleep at night. And, frankly, you'd be insane to invest if you see any of that as likely! IMHO.