I'd start with Vacasa and Evolve customers in your market and unapologetically state that you are new, hungry, and cheap.

It’s the same market it was last year.

Pick a target market (only 1-2 markets when you're starting out). 

They have rehabbed and sold thousands of properties...I think they do a good job of handling the rehab plus they put in "market rate" tenants. 

We do 7-8 flips a year and always use the same local closing attorney.  I'm wondering if it is common to negotiate closing attorney fees due to repeat business for the CA.  When we purchase a property, we have CA fees...

The building has been on the market almost a year and is probably still a bit 'overpriced', although I have yet to do a comp deep-dive with my agent (soon!).

The bedrooms all got rented first month on market and total now is $5500 a month.

Hey Nate, it makes sense to continue building out your investment portfolio in Milwaukee, but if you're looking in the Midwest, I recommend you make sure you get very familiar with the market you're interested in and build your out-of-state team first such as an agent, property manager, lender, and contractors if you're planning on house flipping.I recommend checking out Long-Distance Real Estate Investing by David Greene, where he takes you through how to properly invest out-of-state. 

This should have been an off market listing.

With savings rates so high I'd save in a money market mutual fund until I had enough to get rid of PMI on my primary.