What sort of boat are you planning on (do you have one now?)
I was thinking of a 30' to 35' older boat. I've looked online and there are tons of them out there for less than $50K. I want functional over fancy. For example, I'd be happy with mostly just a head, galley, and hammock inside.
Around here the costs alone to join a 'Royal' club at near-retirement age will buy you a pretty decent boat...
A 3-month Introductory Membership is around $750. The courses aren't all that expensive.
Is this a solo liveaboard situation?
Does your club/or other available moorage locations sanction liveaboards?
I'd leave this area when the time came. I was thinking of spending my time between Montreal and the Maritimes to begin with, and heading to the Caribbean and further afield, eventually.
Budget will have a big bearing on how successful this plan is..
I have some flexibility -- I could wait a bit longer to retire if the numbers don't look good enough. My plan is to go at 62, but I could go at 65.
best of luck with it!
.. and Welcome to Sailnet!