Good input from Killarney, who is halfway around a circumnavigation so knows a bit about this.
It sounds like the sailing part is reasonable and even two straight weeks is enough to have some idea what would be getting into. We have many first time posters who have never been on a sailboat and plan to set off on incredible adventures. Glad to see you're more grounded.
You nationality is going to have some impact on what will be easiest for you and what it will cost. Before I set off on anything permanent, why don't you take a holiday and rent a bareboat somewhere to see what its all about. You just can't lose.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.