Re: Captain for charter?
The Charter companies are probably going to require a Captain, if that's all the sailing you've ever done. Many will rent you a bareboat when you're fresh out of a legit week long liveaboard course. Ten years later, if you've not kept up with your skills, they would understandable worry. Sounds like you may be too.
However, if you think you can handle it and have a bit more experience to show, they may only require that you spend your first day with a Captain aboard to essentially check you out. If you and they find you are safe, they'll let you taker her alone from there.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.