I bet you could make quite a lot with it that way if you're allowed and willing to do the work.All that said, I agree with the posts above that said to basically calculate out your ROI on it and compare that to what you could get with another proposed investment.

I would bet a good number of millennials don’t know how to address a letter.

My boyfriend actually lives in Gravois Park, I feel safe where he lives as well but I agree staying within a block or two of Cherokee and closer to Jefferson is your best bet. 

I’ve seen other comparably sized properties on Airbnb charge this much and much more then my averaged out price of $250, so I think it’s a very reasonable benchmark for me to run my numbers on.

So the lot size will be a lot smaller than it already is.

The cost associated with completing those corrections should be in the contract, but not necessarily spelled out, but definitely absorbed into the fixed price.Depending on the size of the civil engineering company's design staff, it should take approximately 1 to 2 working-day weeks to turnaround a plancheck if the design was done within substantial conformance of the design standards of the governing agency. 

Since banks will only do 70% LTV on multi family non-owner occupy refinances is hard money my best bet?

It's hard to find this size deal in SE WI. 

PMs depend on the size and location of the property.

For a house hack, your best bet is to buy it in your name, then when you are ready to turn it strictly into an investment property, transfer it into an LLC.