We could pay off the house but have been holding onto a chunk of $ to see what (was hoping for some more stock volatility).

I’m glad to hear there are still markets for older properties, since most rental stock in my area consists of homes that are 30+ years old.

If the stock market dips 20-30%, your townhome will likely help stabilize your portfolio. 

If return on equity approaches typical stock market returns, I would lean toward investing in the stock market, as there is less effort involved (though not necessarily less risk). 

I feel I have spent years working on W2 income, investing in the stock market and diversifying, and getting on the right track and staying there financially that I am ready to leverage some money against the future appreciation, value, and cash flow that I am more risk tolerant to put up money in homes that bring a strong future value and promising cash flow.   

Have some real estate, own stocks/ETFs/mutual funds, own some gold etc.

The attached chart is the 10-Year Treasury and you need to watch it closely (“TNX” on your smart phone’s stock ticker).

We end up stocking about 50/50 because my wife will drink my bourbon (she doesn't want her own glass, she just wants some of mine even if I'm not having some).

This Stock versus REI comes up fairly often.S&P 500:The primary advantage the stock market has is Liquidity. 

IRC §351 may allow tax-free treatment if you receive stock and retain at least 80% ownership, but a quitclaim deed without issuing stock usually fails this test.