Good luck dude, sounds like you're well on the way.
I was in what sounds like a similar situation to you. Got the idea of setting sail into the wild blue yonder early last year. Posted a thread similar to the one you just did about mid way last year and i've spent the last month cruising out in moreton bay, last time i was at a marina was a xmas eve. So zero to cruising in a bit over 6 months from starting the boat search and getting the boat took maybe 3-4 months or so. I moved in during september i think. Maybe late august.
And i gotta say, it has been the best thing i've ever done. Cruising is just awesome, so i'm voting for go small or medium or big, but go now. It's certainly possible, though my situation is a bit different as i'm
learning to sail in Moreton bay, which is a sheltered, popular sailing grounds so it's a pretty ideal place to learn. IMO if i was going to be doing an
offshore trip i'd at least get an
offshore sailing course done. Though with your background it sounds like you've got a good set of skills (ie
maintenance,repairs etc) stuff which i'm still working on. Managed to do a few modificiations with
family assistance myself but a big part of my
learning curve before i'm ready to go offshore will be
repair work, especially
engine maintenance etc.
Going from what I've been adjusting too (ie shore-life to cruising, singlehanded etc). Get used to things breaking down and needed replacement etc. The amount of replacement
parts,
repair work and
lost parts has gone from basically zip being tied up at a
dock to quite a list(ie
battery bank needs replacing,
anchor windlass fuses,
anchor light has stopped working,
lost a few things
overboard ^^,
fuel costs (genset,
outboard, main engine), running aground and the subsequent haulout needed to repaint the
keel. -.-, this is all in the last month now that i'm actually sailing and being exposed to
weather, needing to run more systems etc. So keep some dosh spare for when you actually start cruising, there will be
repairs along the way. Something i should have done, but i'm still working while i
cruise so it's no big deal. If you're not going to work while you
cruise or are relying on finding a job once you get there I would really recommend keeping aside a fair chunk of your
budget for just that sort of thing, thats besides the
refit costs.
Besides that, it's been well... pretty cruisy^^. Not having easy access to a convience store makes
provisioning rather important (tis a bother to run out of tobacco when you're half a days sail from the nearest store).
Have fun out there!