This makes them especially popular with multigenerational travel since grandparents can stay downstairs and also have more privacy.

The dilemma arises from the difficulty in splitting up the workload.

I don't know about Chase City, but Green Bay has a rising market.

All over the country "known" markets are getting bid up to stupid #'s (I am sorry if you think a 6 cap is a good position on a SFR, it's not, just facts of it) so it's common sense in a popularly known major market that finding a good margin deal isn't viable right now and even asking for such is an invitation to get scammed. 

I am curious as to which neighborhoods seem to be the most popular right now for flipping houses. 

Now this may sound crazy, but there are actually quality (and by "quality" I mean they get you rent every month & respect the property) C class tenants in Bridgeport - its just a matter of being content with lowering your expectations and being honest with yourself when thinking of if you can deal with the issues that may arise with this tenant class. 

I'm basically the most popular guy in real estate in the area 😎

If you get down to the wire, a DST (Delaware Statutory Trust) is an increasingly popular option as mentioned by @Betty Klein.

I doubt so, but some of my colleagues might feel differently.You may come across a popular notion of "how would the IRS know that I never moved in"?

We have snowmobiles and the lake we're on is really popular for ice fishing.