We went through much of the same decisions. We don't have kids but looked at various boats from 30 to 42 in mono and multi hulls. If
money was not a object, we would go for a larger
catamaran (Antares 44 would be the dream boat). But everything costs more (i.e.
purchase,
maintenance,
storage, etc.).
We ended up with a
Catalina (C310). Its hard to beat them for the value. Our C310 is a smaller version of the C350. It has many of the same features but only one
cabin. It sounds like you are OK with your two boys sharing a
cabin. If that's the case, I think the C350, C380 and C400 would make a good choice. By the way, the C380 and C400 are not coastal cruisers; they are
Water boats">blue water boats.
As to your question about the cockpits, as a
live aboard you spend alot of time in the
cockpit. And if you set yourself up right, that would be year round even in cold climates. The first key addition would be a
cockpit enclosure built off of the
bimini and
dodger. That will allow you to use the cockpit in the heat of the sun, the rain and when the bugs are out. For the
winter the key would be the clear shrink wrap. That will act like a greenhouse and it will be comfortable in the cockpit on a cold, sunny
winter day. We have had as many as 10 people hanging out in our cockpit. I wouldn't go sailing like that but on the hook or in a marina it's fine.
To the timing, I would say do it now. We
mortgage our
boat like a house and the interest is tax deductible. We have a less than 4% interest rate. That brings the payment pretty low. Even when you combine that with the marina cost, it will likely be cheaper than your apartment. It will certainly be cheaper than an apartment plus a
boat payment.
Good luck and fair winds,
Jesse