I would speculate that I have probably listened to 1,000 hours or more of rental, money, business, self-improvement, and related material over the years, time that would have otherwise just been spent humming along to the radio, gaining nothing.

Investing based on speculation is the same if its the housing market or the stock market.

, and others that are turning a corner and may have significant upside if you don't mind a little speculating (Station North comes to mind).  

I understand your thought process of buying during a recession but people have speculated about a potential recession for years now and it hasn't happened. 

Now, people speculate and hedge funds speculate better.

Several of the variables (anything w/ appreciation) are speculative and won't be accurate until executed.

And I know that question can only be answered with speculation until all the events transpire.

The newly created trillions are (a) papering over previous speculative losses and (b) going onto the balance sheets of companies/individuals that simply add another digit to their net worth.  

There was some speculation a few years back that it was heading in a much better direction and there was building and improvements being made and businesses moving in.

Highly speculative and risky but, it is a strategy.