I do feel Milwaukee is a great market, but it's starting to lean a little more heavily towards appreciation than cashflow in the more popular markets, in my opinion.

NoiseAware is also popular.

@Matthew Pinkston, It was nice to meet again and spend some time discussing progress, goals and brainstorming strategies.

Just wondering since your last post, how has your progress been in the area?

They are making progress, but every city is different. 

Classic path of progress stuff in a close-ish market.The other option ( which could be very unpopular) is to sell both and preserve the down payment funds. 

This strategy is very effective, especially on houses with lots of parking and houses with lots of bedrooms and bathrooms in areas near the popular locations around town.Realistically, you can get $750-900 per room that shares a bathroom, and $900-1100 per room that has a private bathroom.

I am sure you can understand that growth is not necessarily a linear progression, and that it takes time to ramp up to that volume.

Also considering a STR in a popular tourist area of my state. 

All homes will cash flow at least 40k-60k per year in popular Airbnb location.