Build a relationship with your local handyman or contractor . 

The only wrench in all of this is that as I am not familiar with the area in its entirety, I am having trouble networking with a decent contractor that I can partner with/hire to help with the rehabbing process.

That would include you or them acting as a third party facilitating a real estate transaction between two other people.If you are only buying properties for yourself to flip or whatever, and these appointment setters are your actual W2 employees and not 1099 contractors, then you are probably OK.If you're a wholesaler and don't intend to take possession of the property, well that could be completely different.As always, I would advise spending a few bucks to talk to a real estate attorney on matters like this.

If you had an established and trusted team of contractors, I would say that there is a tremendous opportunity for value-add opportunities throughout SA.

If you're going to self manage, you'll want to start building a list of vendors, contractors, and realtors to research. 

Hi William, Milwaukee is a pretty interesting market; certain parts are great to invest for long term wealth, some are growing, some are redevelopeing, other parts are cheap and perfect if you are looking to cut your teeth on some issues.

Look for a new contractor.  

Personally, i would not be willing to got to that extreme for several reasons. 1- dealing with the city, inspections/permits, and contractors you're talking about serious renovation.2- is the RETURN worth the investment?

You wouldn't want to expose the rental assets to the risk of Flips ( contractor falling off the roof).

Plus my local network of contractors.