Most people would agree that it's a good idea to invest in real estate because it is a tangible asset and you have control - compared to the stock market, where you have very little control.

., I think there's a lot more to the bay area tech than publicly traded companies compared to last time.

If it makes you feel better you can run a computation of your planned purchase and estimate 20% down and then recalculate your amortization if you want to compare apples to apples. 

My contractor who replaced laminate for the stairs claims that he remembers it being around 36 inch (as compared to 30 inch as per building code).

I compare REI to poker all the time, but my comparison is that the number one rule is the same for both, "you must stay in the game".

Some of them I am not too keen on keeping due to age (75 years and counting) and the amount of maintenance they required compared to newer properties.

Maybe there is a comparative loose piece under the house I can break.

The announcement of a new hospital near I-90 and a hotel downtown will help as well.Home prices are climbing a little in Rockford but are still very low compared to the suburbs of Chicago.  

Comparing Bank Recourse debt to Agency Non-Recourse debt, the most significant difference might be Replacement Reserves.  

Run those numbers long term and compare.