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Originally Posted by GraceForDrowning
Enjoying reading a lot OP! You hear a lot of people complain that doing stuff like this isn't really possible while at the same time spending half of what they earn on paying interest for cars and apartments/houses that yield little happiness. It's nice that people like you prove them wrong.
Do the house owners favor your profile (couple, in a "good" age) or is it possible for a single man in his mid 20's to get into house sitting as well? I would imagine girls have a much easier time.
It's definitely possible. You just got to want to do it.
Honestly, it's really tough as a young male to get a lot of opportunities, but not impossible. You are unlikely to get the great house sit jobs as you will be up against too much competition. For example the house sit in Barbados we are doing had over 80 people apply for it. If someone has a choice between a middle age couple and a young guy, then 95% of the time they are going with the couple. But you don't have to be in a couple. My mother in law is in her 50s and gets house sits a fair bit. She has real bad arthritis and moves around like a snail. People like her because they know she will never go out and their house will be occupied all the time.
That doesn't mean you can't get them. You just got to sell yourself as someone who isn't a party animal and because you are a young male you can fix stuff around the house if something goes wrong. If you have a good profile and talk about being the captain of the chess team and you use to be a handyman, you might have a chance.