I would prefer not to be a landlord, especially since I live 2 hrs away in NY, but it is technically doable.

And spend my time working on the things I'm good at.I think they ARE valuable to have, especially if you're looking to raise private money   We live in a digital world now and anything you can do to set yourself apart can't hurt!

How does this work for the other co-owner of the property that does not live here as a primary residence? 

My property only has $140K in equity but I don't have any other debts, she of course is paying about $800 a month for her pretty car. 

For example, in about 1 year both my car loan and student loan will be paid off.

Hi @Luke Carl - I didn't know all lenders offered vacation home loans, so I appreciate you sharing!

There have been some issues with trespassing in the backyard and car break ins and recently there was a couple of incidents or attempts of forced entry.

At least do an eggshell in bedrooms and living rooms, satin in hallways, entryways etc.  

@Jonathan Greene I have family that lives in Mississippi and I go out there or at least plan to go out there twice a year.

Assuming you aren't doing this full time from your yacht sitting off of the US Virgin Islands you will be busy during the day living your actual life.