In short, he's headed places so he could be a good dude to model after.Secondly, check out the Bigger Pockets Money podcast.  

I suggest a tighter budget and a side hustle to generate some additional income for the short term to pay down consumer debt.

In short, focus on increases in income/value relative to costs, not just gross value added. 

Be ready to give a very short, clear, easy-to-understand answer to: "What kind of returns do you need to hit for a deal to make sense?"...

I would not be opposed to managing it myself for the short term but like you said, w/ prop. mang.

There are certainly some advantages to short-term rentals but just keep all aspects in mind.  

Reading a bunch of these articles and comments we forget these tenants are also our customers if they are not paying and it's the first month that they've done this often times some Grace is allowed especially if they are communicating the situationbut if they're doing this frequently and not communicating and likely short paying every month then quickly move to have them effected each state or province has their own system best to research that or hire a paralegal

Seems like the good ones also have pretty short buyers lists...

While I wouldn't give a tenant a discount for stating they will stay longer than one year I wouldn't entertain renting to another tenant who is guaranteed to be a short term tenant for a nominal increase like this one.

We haven't researched it much yet but I've thought about a short term rental (like air bnb) on either Lake Holcombe or Lake Wissota and those are right in your area.