Meet with a local banker & schedule a time to talk with a mortgage broker, they'll give you at least a baseline of what kind of down payment options and rates are out there.After that, if you're still wanting to research more creative options, do some looking into seller financing (a very hot topic with good, and bad, advice out there), look into private lenders, and commercial financing options.If you're wanting to live in 1/4 of your quadplex, then conventional residential loans may in fact be your best option as you can purchase that with a fannie/freddy loan with very low down, and use up to 75% of the income from the property toward your own income. 

As you can see, two people already said just in this thread they have 100% occupancy during the hot time.

This is one of the things that sound a lot easier than they are actually done.The crazy thing I learned about these CA fires is that the heat radiation is hot enough (1500-2000F) that it will ignite your furniture through the windows.

The seller must think he is sitting on a really hot property, or the buyer is asking for too long of a DD period.

I know some might disagree.The challenge is if someone applies and meets all your criteria and you reject them, I would hate for you to end up in some legal hot water.

Adding a 1/2 bath, new roof, central air or other typical improvements will increase the value of the property. 

We have used actuals and projections from air dna to come up with rent.

That number seems high but the neighborhood was “hot” and houses sold really quickly.What I cared about most was completing my second deal to gain experience.

That has informed us for this year's trip, and we'll be staying in Langosta/Tamarindo, Potrero/Flamingo, and Hermosa (Guanacaste not Jaco).Of course, there are tons of beautiful places in CR, and the better climate (read: less hot) is found at higher elevations. 

-Structural (foundation, wall, ceiling and floor)-Roof and Exterior(Roof Condition,Gutters and Downspouts, Siding, Windows and Doors)-Plumbing (Water Pressure,Leaks, Drainage, Pipes)-Electrical (Wiring,Outlets and Switches,Breaker Panel, Lighting Fixtures)-HVAC(Air Ducts, heating and cooling)-Water and Moisture Issues(Attic, Mold and Mildew)-Kitchen and Appliances-Bathrooms-Pest and Insect Problems-Safety Features