Re: Should I spend thousands on lessons, or....
Generally speaking the best sailors learned on dinghies or small keel boats. You get a much better understanding of balance, sail setting trim etc. Also you are controlling the boat not just acting as the crew or letting the autopilot do all the work.
On big boats being a volunteer is a great way of getting experience but it depends on the knowledge of the skipper. I remember setting up India's first professional sailing school. Some old buffer with no qualifications had been teaching the locals for years. I was shocked to hear he was telling people to go head to wind to drop a spinnaker!! I did a years worth of deliveries before doing my Yacht Master. I gained 10 thousand miles, learnt how to navigate, keep watch and realize I don't get sea sick. However only the skipper was allowed to park the boat and I can count on one hand the number of gybes we did. Great thing about sea schools is that you can get loads of practice doing all the tricky parking stuff and know the insurance is in place. The other tricky thing with learning yacht sailing is the choice of school. Even good schools have less proficient skippers or you may end up with students you do not like.
In my teaching I get people through the basics and make sure they do not pick up bad habits. They often want more lessons but at that point I saw no you need time on the water then come back to brush up the finer points.