We own a property in the mountains on 2 1/2 acres that has 3 houses with 9 bedrooms and can sleep 24 people.Our second house is on the beach off of Playa Avellanas.

Too many people are sleeping on this.Kentucky Economic Development has many site ready properties in smaller areas that are ripe for rentals. 

They wouldn't be coming to you.So you can get a gold standard investment advisor and give up .5 to 2% of your return, or you can send the money to one or more huge index funds like Vanguard 500 index fund and sleep well at night.But if you think you have something of value other than the generic value of money, you will be sorely disappointed.

I plan on converting the barn into another sleeping space and indoor/outdoor rec room.

Many Airbnb guests will want common utilities unless it is in a remote are where you go as a sot to sleep while hiking the area. 

And don’t sleep on local banks or credit unions—they sometimes offer flexible portfolio loans that could work for a deal like this.Since your wife qualifies as a first-time homebuyer, check out any state-specific programs or HUD options for down payment assistance.

Challenge: It's in a neighborhood (no HOA), and renting the entire property (sleeps 25 in total) caused problems in the neighborhood, due to noise and parties – so we only rent the separate cabins now.

Is there a defined definintion of occupany that mandates a set amount of days per month that I must sleep under the roof of my primary residence?

Especially in the winter in heated apartments if they can see a warm place to sleep they are going inside.

Hey @Jonathan Baptiste, so we are a bit different than some.We have a large house that can sleep 12 comfortably and we provide a lot of stuff.