You can do it. But how you do it depends on you and how dedicated you are to doing it. We bought a 42' boat not ever having owned a boat before. None, nada, zilch. I had taken some basic sailing classes and been rail meat on a few racers before that. And decided to buy a boat and figure it out.
It worked for us (my eager wife). But it took far more money
than we budgeted. I got a full time job at a boat yard as an apprentice to learn about boats. I have always been moderately handy but self-taught with tools, motors, etc. But the boat yard put me over the top. You could do it without that but you will need to pick up the same basic skills.
Get ready for the biggest intimidation of your life. Worry about not knowing what you will need to know. Worry that you don't even understand the words you hear/read on sailing and sailboats. Worry about wrecking the boat. Worry about weather
. Worry about others thinking you are crazy. We all worry about these things, or at least a fair number of us do, so you just have more worrying to do to catch up.
Go sailing on some boats. Ask questions like a little two-year old "why, why, why"..... Charter a boat for a week somewhere. Hand out at marinas
and ask people how they got started and what the hard parts
So buy your boat and put an equal amount of money
away in the bank for no other purpose than to use to prepare the boat. No drinking or eating with this money. Buy a good basic tool kit. Take as many classes as you can on diesels, outboards, sailing, plumbing
, electrical wiring
, etc. Long list. Start reading every magazine and book you can find. Get a West Marine
catalog and start browsing through it (that'll probably kill the dream right there).
And then take baby steps. Take the boat out of the slip and put her back in. Drink a bottle of booze to calm your nerves and steady your legs after you do that the first of many times. Just motor
around and get used to the boat under power and in different wind
. Put up the sails
and take them down. Winds are not often not good up here for sailing on any given day so we motored a lot, and still do. But that took the major fear out of that part of it. And we only had to worry about one subset of the boat to start with. We never really learned to sail until we went offshore
But depending on how much you know to buy a boat with offshore equipment
, you may find you now have to start adding on or upgrading stuff for going offshore. This is after you have fixed the broken stuff that you need for local sailing. That's where your boat kitty becomes really important - depending on how much "luxury" or "high tech" you want to go off.
But for whatever sake, talk to some people who sail with dogs before you go do any of this. Your dogs may hate you forever and you may hate either the dogs or the "sailing with dogs" forever.
But can you do it - sure you can but it will require a humongous effort and will. We just bought our second offshore boat and I am re-intimidated all over again. And I wish I still had a big prep kitty in the bank.