Out of curiosity, where in CO are you located?
As for maintenance
experience, I don't yet live aboard or cruise
, but I have found that attitude is more important than anything. Sounds cheesy, but with the right attitude you can learn to fix or maintain just about anything, especially given the resources (this forum is a great one) available today. You just have to be curious and unafraid to get your hands dirty, crawl into dark/dank spaces, and maybe even get someone else's pee on you from time to time.
If you don't already, start doing as much of your own maintenance
and repair around your house, on your vehicles, lawn equipment
, snow mobiles, etc. as possible. It'll boost your confidence and keep you in a more mechanical mindset. You'll also probably start to see that, generally speaking, things usually aren't that complicated.
When not skiing, I'd recommend spending your winters reading not only about sailing, but anything you can find regarding diesel
engines, electricity, plumbing
, etc. In time, you might even be able to find an older boat with a diesel
inboard on Lake Dillon or Blue Mesa. Doing so would get you hands on experience with many of the same systems you'll be fixing and maintaining when your dreams come to fruition.
In the meantime, however, just go sail paint
off of the Sunfish and don't forget to have a blast doing so. You'll eventually look back and really miss the simplicity and purity of the days you spent on it!