If it's a deal that is in a very very desirable location and has tons of built in equity and appreciation, I would be totally good with negative cash flow for Y1 and Y2.

My answer would certainly be highly dependent on his own emotional make up, his desire to relax and travel, his willingness to delegate and outsource, etc.

I get the desire to own outside of Chicago proper, but instead of going to another state altogether, why not invest in one of the burbs?

There are other ways to legally raise capital, however, they have some inherent disadvantages making them considerably less desirable for what you’re trying to do.   

The new design takes the home from a 3 bed, 2 bath to a 4 bed, 3 bath, 2,400 sq ft rambler on a large lot in highly desired area.

Just the other week I was giving a tour to a potential Canadian investor, and they were shocked at how quickly a street goes from mid/high-end to....well, not as desirable.

Choose the Right Property:When choosing a house to flip, search for properties in desirable neighborhoods that need structural or cosmetic improvements.

Still has lots of belongings (including a boat) in a large shed on the property... could imply intention to move back, or a desire to not have to deal with it and possible interest in having help getting rid of all this stuff3.

I desire to begin investing asap so I started the process of  learning as much as I can by reading and watching videos.

For instance, do 2/2 properties typically have longer average stays, or are they more desirable?