Check out this volatility chart showing the largest gains and losses for different asset classes over 1, 5 and 20 year time periods. 

Taxes are volatile in CT, especially in Hartford.

@Kevin Blanchard I respect an appreciation play, but there isn't much weight to it when you're buying in a volatile city at the top of a market you know?

Within C class, duplexes are much more volatile than SFH's.  

Crypto is too volatile, apps like Robinhood those that allow you to buy individual stocks would not align with your goal right now so I would not focus too much on those.

I also like communities with robust healthcare networks and universities as both aren't as exposed to economic volatility. 

Income is good right now (500k+) but in the mortgage business as you all know can be very volatile so I am paranoid about being house rich and not having enough cash.

Alternatively you can also use the Fannie Mae underwriting guidelines to determine the actual net income (75% of gross rents - PITI(M))The advantage for the seller here is, that he will receive (almost) the same income without any volatility.

Both are positioned to do very well over the short- and long-term, for whatever that means in our volatile market...One more thought: analysis paralysis is the enemy, far more so than choosing the "wrong market."

As long as we don't have a huge set back with Coronavirus or epic stock market volatility again it does seem like it should just be a matter of some time.