Re: Reassurance and your thoughts?
Same thing, bought the boat, then learned to sail. I got most of the information I needed from books. The wife and I had one day lesson, Just to learn what all the ropes do, and a few other things that the books just don't make clear enough. Having said that I had a fair bit of knowledge before taking up sailing. Used to do a lot of fishing on a 17' power boat so knew the rules of the road etc. I've used radio's most of my life so VHF was not a problem. All of the sailing knots I use on my job, so again not a problem. As far as navigation is concerned, well I've done a lot of land navigation ( and no I don't mean road maps, I mean orientation). Making the switch to marine navigation was not that difficult.
All in all in can be done. But you've got a lot of reading to do this winter, and perhaps a lesson or two, or three, or four might not be out of the question.