These properties cover my mortgage, allow me to save for maintenance/repairs, and are projected to be worth $7–9 million by retirement.

I wonder if it's worth it to sell shares pay the 15% capital gains and pay off the mortgage.

Owner carry financing, hard money for renovations, then refinanced into a long-term mortgage.

However, if your mortgage allows open prepayment to an annual limit and/or an annual payment increase (as do most fixed mortgages in Canada), then borrowing from the LoC to prepay the mortgage serves little purpose unless your LoC was on better terms than the mortgage.  

After some issues with the mortgage lender not doing their due diligence until the last minute they put in some of their commission to support the closing of this property.

Conventional owner-occupied mortgage rates are above 7% today (source: Mortgage News Daily - Mortgage And Real Estate News).

I'm a commercial mortgage broker and I'd love to connect to discuss debt financing strategies as you come across potential deals. 

I started out with a house hack, and I would say that that was definitely safe for me when I was in college as I could afford the Mortgage even if my renter didn't pay.

Using mortgage debt at 6-7% on a refinance to pay off higher rate debt such as a credit card at 15-25% is a savings!

Maybe you saw this from the Tico Times already, but it lays out mostly depressing details on getting a mortgage in Costa Rica: http://www.ticotimes.net/realestate/25-mortgage-ti...Please post back here if you find anything!