Welcome! I'm in the "just go for it" camp, but it does depend on your personality because if every problem you face breaks you down a bit more, rather than build you up as the learning
tool it should be, then you will find the boat gets used less and less. Sail as often as you can to build confidence, take it easy when you try new things, bring experienced people on board when you can, shrug off the times you come in scraping the dock
, put out big fenders, think ahead three steps before you act, and always remember it's just a bunch of epoxy
as long as no one gets hurt. Above all, have fun.