I have flipped several properties and have some rental properties, but I have never done a 'Subject To' deal. My realtor just brought me one and I was wondering what everyone thinks.

It's a 1960s rambler - 3BR/2Ba on a lake and right across from one of the top golf courses in the state. The landscaping outside it beautiful and it is on a dead end street in one of the most expensive towns in the state.

It needs to be updated with a lot of cosmetics - I'm estimating about $40K max. The owners would probably let it go to me for about $400K and the comps for it support $525-$550K.

My questions would be:

1) How do I find all the documents to set up a subject to transaction?

2) Is this a decent deal? What kind of questions should I be asking beyond the basics I have here?

3) Would it make sense to rent it out on some kind of vrbo (vacation rental by owner) basis through the long Minnesota winter and then sell it in the spring, or try to sell it right away?

Anything else you can think of that would be helpful?