Business/RE friendly government- Sunshine- Other transplants and a welcoming communityDoes this exist anywhere or am I looking for a unicorn?  

I have a three unit in Irving Park close to the blue line and a four unit up in Edgewater. 

And a side question - what would be a fair split for someone only signing the loan and not supplying any capital?

The full-time owners had an outsized voice on the condo board and did not like the fact the we and a couple of other owners were renting our places to "transient" residents.

It's been her primary residence for more than two of the last five years, but it has also been an investment property for the last year and a half while she's been stationed overseas.

Get documents from the contractor - a contract with the scope of work, an invoice and a payment receipt2. 

A tiered offer could look like this:$900,000 with 45 days due diligence, 30 days to close and a financing contingency$850,000 with 30 days due diligence, 30 days to close$750,000 with a $100,000 non-refundable deposit and 30 days to close

I can also tell you I was able to glean some helpful information on the probate process/law simply by calling the County Clerk's office and a local probate attorney and asking very specific questions about the process. 

You cant be an owner occupant and a "wholesaler" of the property at the same time.

I would walk the property with a general contractor and a realtor.