This determines instantly if a lender will touch it.Another factor: STR financing is getting harder to come by (at least in the DSCR space). 25% of the industry used to lend on STR's, now it's less than 10%.And it being a condo, expect anywhere from 15-25 bps added to the rate.

If you are in the industry then you already have the connections.

During my time in the industry I learned to work systems so that I could consistently effectively list homes to get them sold in a timely manner. 

We've been doing it this way in the construction industry for decades.Best way for you to know what's it gonna cost for your projects is get estimates/proposals from licensed contractors.

The tenants are paying 150 dollars less per month then an average 2 bed 1 bath apartment rents out.

They are the Hamas of the real estate industry IMO.

Racine would likely be a better "sell high" plan since those property values on average are 20% below Kenosh at the moment.

MTR is strategy here with the industries we have.

You could also call a couple of contractors on the phone and get rough sqft pricing from them for roofing, siding,  painting etc. like how much the averages costs are per square (100 square feet) and square foot .

I would consider buying a duplex, tri or quad as a primary residence and move into one of the units and rent out the others.You could sell your primary and use the capital, or pull the HELOC and use to buy a small multifamily.You can also learn how to flip properties to generate additional income to use to buy properties to hold longer term.You can also consider looking into a job in the real estate industry, such as an analyst, broker, lender ,etc that can get you in the gameAll the bestGino