You find a fixer-upper to Rent until you Sell and just move into the Rental to do it again. 

These designations are typically used to get a leg up in the employment world but also serve as an excellent source of education. 

Real estate is often described as a 3 legged stool... with cash flow, appreciation, and mortgage pay-down all acting as legs that let you build your wealth.Plenty of people will say, equity plays are fine... and they can be.... but they come with higher risks than a property that cash-flows where you have extra income every month to help pay the bills.  

During that time you find a fixer-upper to Rent.

It also has a large flat upper roof area, although not sure if it could be used for something or not. 

@Zachary HarrFellow Midwesterner (from Upper Peninsula of MI) and was also pretty low income. 

You can't conclude that Nike's shoes are worthless because no one engages with Nike's ads when they are displayed in front of people without any legs.

My girlfriend and I are interested in buying into the upper Michigan STR markets (Traverse City, Charlevoix, Petoskey, Bay Harbor, etc), hoping we can take advantage of the hot vacation rental market up there in the summers and the popular ski slopes for the winters. 

A handy search bar in the upper right makes it easy to find previous discussions, blogs, podcasts, and other resources.

Additionally, and please confirm this, I don't believe the HCV system increases their upper limit every year.