Hi rocket pj from another BC Coaster! Aahh sailing. You've covered so many truths here: the split between the possible dirt-cheap freedom lifestyle and the ultra-rich toy world, as well as "But the work/kids/savings/time/business conflict is too much, and something has to give". And the exponential cost increase of bigger boats. Sigh.
We started in an Alberg 23, one of the cutest, solidest, most fun little boats ever. We bought it for $6500 and it cost us about $200/mo for moorage. It was a blast. Sailing is my husband's ulitimate passion in life, and he is still pinching himself that he gets to be a sailor at this time in his life (he was 45 or so when the dream came true after MANY years of us dreaming).
A couple of years ago, we had an opportunity to scale up to an Alberg 30 in GREAT shape for $7500 as part of an estate sale from a family we knew. Standing headroom! A toilet! A galley! A dodger! Heaven. We sold our smaller boat to a friend in a flat market for $5500, and then needed to do some work on the new boat...Now, between moorage and maintenance, we probably spend $550 a month. On something totally superfluous. The hard core mustachian in me cringes regularly; it's not like we're anywhere near FI.
And the time crunch is tough too, sometimes. We are doing the homestead thing, and the pull in good weather between sailing and the garden/house is definitely a source of tension. Especially because we have clown commutes and our time available is pretty limited.
On the other hand, my DH would rather sell the house than the boat. The boat is his passion, his community, his destress hobby, our cheap "escape pod" (if the SHTF we could live aboard in reasonable comfort), and very cheap regular vacations short and long. It adds a lot to our lives and it would take a lot to walk away.
So...we just use it as much as we possibly can, and we live with the very imperfect balance between costs, plans for the future, work-life balance, and finding joy.
And then we regularly pinch ourselves for all our first-world problems! :) Life on Vancouver Island is awesome. ;0