Owning a Vacation Home in Caribbean

Warning:  I feel like ranting a bit... Our vacation home purchase has been a sometimes frustrating and almost always exciting endeavor. Once my husband and I determined that we wanted to try living on a tropical island, we enacted a plan to make it happen. We aren't there yet and we see different paths forward but it always boils down to money.  Here are our options with pros and cons: Option A:  Cash it all in and go for it! Option B:  Use the house when we can, rent it when we're not there, retire in 8 years with my teacher pension (if it's there for me...) and a maintain the 3 rental houses for passive income. Option C:  Semi-retire in 2 to 3 years, take whatever savings we have to buy and renovate 3 to 5 more rental homes in lieu of my pension, and have the passive income now instead of later. I would love to do option A.  But, I have children in school and although I want my children to experience another country and really get an international perspective, I

Unfortunate cloudy day...but, the extra suite now has a door to pool deck! The Master At Work...Peek A Boo! It's 3 AM. The WhatsApp notification chime has pinged twice and awakened me out of a much needed restful night sleep. My heart is pounding. WhatsApp generally means the neighbors at the casa are contacting me about something... tinaco isn't filling, no outside lights are coming on...or the worst...the bars have been pried open and the house is standing open!?!!! Holy S@$#!!! (That actually happened... I'll elaborate in a future post about safety in a up and coming non-touristy town) But, wait...no, it's a message Judy sent earlier that day during a internet outage that has just now come through to inform us that our normal cleaning lady couldn't make it so she had gotten her lady for the house before our first ever renter arrived!  PHEW!  Cut to today, my darling husband is on one of his lone trips down to the DR and doesn't understand the 1 hour