I've been hearing a lot of people re-fi'ing 3 mos after purchase.....at Brew City REI Club's last event, a lender said he could re-fi off appraised the day after purchase but you'd have to show that you did repairs. 

Most people have a mortgage on their home when they sell it.

This tells the algorithm that people are interested in booking your property, even if they don't book it. 

People realize they are not going to get 1/3 of value whether it takes a month or a year because of holding and closing costs.

It's not a get rich quick scheme, it's a lot of active work and I would have 5 yrs in my head at a minimum before you truly become established and stabilized. 

Neighbors activity or their poor unit maintenance affecting your unit or tenants.

If you have an active root...over time it will grow back in there unless you excavate, cut and remove. 

How many people do this?

I also want to be active in other rust-belt cities that are similar to Milwaukee and I want to be part of their eventual comeback: Cleveland, Detroit, Pittsburgh, St.

Its worth having your brokers license if you want to make money helping other people buy and sell.