My goal is to live in the home during the winters, maybe 3-4 additional weeks for vacation, then rent it out to help cover the mortgage the rest of the year.  

They wouldn't be able to get a mortgage, but would have to do some kind of SBA loan or other commercial loan for the business with the properties as part of the business.

I have a mortgage on each building.

There's obviously opportunity here to build this out and turn it into a basement apartment, which I think would cash flow because of course there's no mortgage. 

Hi Aubrey,International lenders don't exist for real estate in that no lender in one country will give you a mortgage loan in another country.A good service to estimate revenue in Costa Rica or everywhere in the world for that matter is Aidna.

It's an estimated cash on cash return given current rental rates subtract expenses assuming 7% interest rate, 10% management fee, 5% repairs, 5% capex and other expenses like mortgage, insurance, tax. it's a estimate to tell you what properties to analyze vs ignoreyou can see the are pockets of negative returns as well as pockets of positive return. this is to supplement the data @Devin Conley provided

Ouch@Brett Synicky the scenario was if I could find a house and pay for it using the IRA then that would become the mortgage.

I did the math and could cover the mortgage solo if needed.

Everyone will tell you it’s great to get started early, or you can just move after a year, but in the current environment in our region the rent your property will generate after you move out will likely be less than your mortgage, if you are tied to the area and feel confident you want to stay in whatever property you buy for 3-5 years go for it, if you want flexibility rent and throw that money into and index fund. 

I rented out two rooms in my house to help offset my mortgage.