@Will Barnard you're right, it was a very short post without much clarity or explanation.What I meant to express to @Joshua Jackson was that I don't think it's a good idea for a new investor looking to get into buy and hold to pick up a residential rental property in one of the country's most volatile real estate markets, during a peak economy (which has been extended artificially moreso than any bull market we have seen in our lifetimes due to multiple rounds of QE- now called POMO), with a long with a long term hold strategy. 

Part of what I like about Milwaukee (from an investor's perspective) is its slow change regarding neighborhood shifts--perhaps it is an illusion but it feels less volatile to me as a result. 

Anything happens and I have cashflow and reserves to weather any market volatility or interest rate issue once refis are needed on the commercial property.

Overall it’s on par with the returns of the S&P 500, with far less volatility. 

Up and coming is a tricky concept - they are by definition volatile areas, often driven by speculation or the anticipation of a major investment or new business.

Watch out for the Housing crash Zach,no doubt the economy will be volatile, but housing country wide should stay very strong.

I am making many assumptions here, but I am mostly assuming that you will need the cash flows from the $30-$250k to live on.In my opinion, the stock market is too volatile and if we have a sudden downturn you may not have enough time (thinking 10 yrs +/-) to recover from any drop while maintaining your current standard of living.

Also, some markets are more volatile than others.

I would need a trusted RE agent, to learn how to properly evaluate a potential property, how to quickly analyze repair costs, find a reliable handyman/contractor, analyze if I need to use a PM or to self manage and all that is entailed with that, learn to fully maximize rent, and the list goes on.This just seems like a steep price of time and effort to get into a market that can be volatile at times.

I would still probably recommend a first time investor not jump into a market that is known to be volatile in an industry that is not liquid.