I am 50 years old and lost all my retirement money in the crash.

MY reasoning is they have had their formative years in a low interest rate, low inflation period with a major real estate crash. 

Many people who did this before the crash ended up losing both homes because they could not cover the mortgages.

Given that it has been ~ 8-10 years after the last crash, does this imply  that this city has no good appreciation potential?

When the market crashed we were at the tail end of the rehab. 

After the crash they let the prime money pump it, when that runs out they let the average money pump it, when that runs out they let the subprime money pump it..If you are a prime borrower, great, you get to buy the dip right away..

The app kept closing when I hit post so I thought it was crashing and not going through.

Hold onto cash for the crash" - Investing $100 after the crash is the same as scenario A above. 

@Jean Pierre Assaad now that the market has climbed since the 2008 crash, there are not many markets that are under $50K properties that are not high risk areas. ($50k meaning all in price after repairs). 

I am about to list a place for an investor colleague of mine in Forest Park that has literally appreciated 200% since he bought it during the crash.