You've got the right plan... join a club, get some experience and maybe even some cruising time if you make the right friends.. but.....
What sort of boat are you planning on (do you have one now?)
Around here the costs alone to join a 'Royal' club at near-retirement age will buy you a pretty decent boat...
Is this a solo liveaboard situation?
Does your club/or other available moorage locations sanction liveaboards?
Budget will have a big bearing on how successful this plan is.. best of luck with it!
.. and Welcome to Sailnet!