Should I hold onto as much of it as I can and bet on a combo of cash flow and appreciation for the long term?

I would not, however, bet on shipping rates staying this low over the long term.They have all the plumbing and electrical built into a centerpiece.This the sort of problem you'll face.  

Always happy to see new investors jumping into action versus standing on the sidelines.  

You bet--i sent you a connect request w/my info if needed--best

That just tells me real estate must just be a safer bet than dental offices from an investors perspective, which is great as I'm moving away from dental.

Johnny, I know exactly which lender your working with.I am going to tell you, there are better options.Look around a bit, That prepay is 5% fixed for 3 years.I wouldn't pay 22k to buy a rate down in a decreasing rate environment.A 7.75% on a 3,2,1 declining prepayment is a better bet. 

As for the move-in fee versus security deposit issue, many landlords prefer security deposits for better protection, despite the extra steps required in Illinois.

CAR forms and attorneys are going to be your best bet.

Honestly, big banks have terrible rates on mortgage.Work with a broker, they are your best bet; pricing beats big banks 9 times out of 10.

Also adding in here for anyone else viewing that we would need to consider the possibility of the IRS classifying this as a second home versus an investment property and disallowing any potential 1031 exchange due to allowing a family member to use the home rent-free.There are safe harbors to qualify for a 1031 exchange.