As someone who is considering ownership at some point, one of the primary cons for us is that our boat would be used by so many unqualified captains. However, as you state, the requirements for bareboating are unlikely to change. The idea of building the knowledge of those who are chartering the boats is better than the alternative - unqualified captains with little to no knowledge. I grew up driving large offshore fishing boats, but it was still a lot to take in when we went for the first time - even with the briefings. I would have appreciated someone with years of experience teaching us some things online prior to our trip.