So my situation; I've made almost 100k for the last 8 years, but badly mismanaged my money when I was younger so all I have to show for most of that is bar tabs and memories. 

Many fond memories.

If you're looking to get the best ROI, I'd advise you to not use your "vacation" home for personal use.If you want to create great memories and defray the cost of your dream house, then I'd advise you to buy exactly where you want to stay.

@Turner WrightAn owner financing agreement between buyer and seller should always be memorialized in a written document that includes the specifics of the deal.

Also, if there's nothing in the record memorializing your claimed interest in the property your "partner" may be able to sell or mortgage the property without you being informed. 

Partnerships have the lowest audit rate, and there is some flexibility in what you can write off (legitimately, not in a gray area) if properly memorialized in your operating agreement.

@Jorge RuizI have not used any of those 4 nor have I heard anything negative that sticks out in my memory.

REO's have a good memory and will recognize your name if you're dropping deals with them over and over.  

I like the idea of providing housing where families would enjoy creating memories in.

Hi Folks, I am a resident physician at Columbia University in NYC and will be moving down to Miami, FL on June 15th of 2018 to start the remainder of my residency in anesthesiology (3-4 years) at Jackson Memorial hospital and surrounding hospital systems.