Vacation Rentals are different but seek out the people who have done them, they are on here (BP), search vacation rentals or VR as they can be know you should find a ton of overwhelming information.

The Power of Leverage: Real estate mostly appreciates over time, either at the pace of inflation as they are a tangible asset, or a fair bit above it when demand outstrips availability.

Consider that he could probably hire a property manager for a lot less.If you can convince him, more power to you...but you should be realistic about what your cash flow will be (it WON'T be $2000/month), so that way you can set realistic expectations with the owner as well.Also keep in mind that if you don't have an equity in the property, it may be illegal for you to property manage it (depending on the laws of your state).

I don't want the island to overwhelm, but make a statement and provide seating.

Those are some pretty powerful motivators. 

It sounds like a power struggle at this point.

It is a very simple, yet powerful name!

Go play around with some retirement calculators and see what the power of compounding interest will do for someone of your age.It makes it harder to spend, when you actually see what it costs you to spend it… And once you actually understand money.

I might even fix up the electrical enough to get power up, since I can do all that, and the cost of materials is next to nil, and that will enable me to run fans to air out the property, power tools to do the "puttering around," etc.2) If that fails to make it attractive enough for a cash buyer, offer the best terms possible to minimize the rehabber's out-of-pocket expenses and facilitate the easiest deal.

From first sight, they look like the same tree types used for power lines, but I’m still researching to confirm.My thoughts were to price the timber on the property and use it to cover the cost of purchasing the land.