The problem with that in any country is that one has to get the government involved from the start, which increases over heads to ridiculous extent.

@Michael LaRocca Milwaukee is a pretty dense market and there is a wide range of properties/areas to choose from. 

This investment should be a diversification of their assets by putting portion of their net worth.If you can also contribute towards the project to some extent financially; then that can give confidence to the 2nd lender.Even it is second position; record mortgage, add them as 2nd lender on property insurance.Keep them updated on regular basis on the project.

Im in the top 1% of agents nation wide (Im not saying this to brag, but rather to tell you how I got here). 

@Tom LiuCall an exterminator and find out what the extent of the damage is. 

Since most sidewalks aren't more than 10' wide, this will be more difficult to do moving forward. 

We are pretty handy people so we were thinking of rehabbing our first fixer upper on our own and using a refi to get the best rent rates we can (depends on the extent of the rehab).

Looking at my available sources, tax records have the house at like 34k, Zillow has it at 75k, and that’s the extent of my research so far.

I marvel at how wide the opinions on as far as where to dump your initial eggs into.

You can definitely build along the way to a certain extent as the first people on your team can help recommend the others you might need.