It's a quicker way than having to deal with the seasoning of a normal conventional loan which is usually about 6 months.

You MUST season the property for at least 6 months to do this. 

I decided to list my rental property as a long term rental for the off season, and a short term rental for the on season (I’m only doing this for the first year, and then I will be doing STR year round).

My wife have been seasonal but are also moving to the area full time next year.

Purchase price: $157,000 Bought property in 2010 at auction; painted & new flooring throughout, it has a large outbuilding that we still use for storage.

I have an option with a local bank but they want 25% down (won't allow a bridge loan to brrrr my money out without a 6-12 mo seasoning period) the rates are much higher than freddie/fannie loans (5%), and I believe they will only do a 20 year amortization.  

For seasoned investors who can buy all three, I think it's a great idea, but I don't like it if you can't get them all.

It's close to home (2 hours drive) and has things to do in all 4 seasons How did you find this deal and how did you negotiate it?

The selling realtor mentioned that they had to remove the "kitchen" cabinets to convince the lender that it was a non conforming storage unit. - What sort of risk am I taking by taking on this property?

Just make sure to get some seasoned folks with the same values as you.