When we
cruise, our monthly expenses are closer to 4000. That's not full time, but it's full time for several months. But we definitely don't skimp, we have occasional narina/mooring nights, occasional car rentals, etc. We also
motor far more than we'd like because we are on a schedule. We could easily dial that back to $3,000.
As mentioned up thread, the cheapest upgrades are the ones the previous owner does. Our boat is loaded with features that I would never have actually paid for, that had very little impact on the purchase price of the boat. But they do need to be recent, if they are too old they still need to be replaced (our life raft was already expired when we bought the boat four years ago, and now it is even more expired)
I would consider pushing up your purchase budget and down your
refit budget. While not really in your price range, our 43 foot boat from 1998 was truly
offshore ready for $140,000. You could probably get a nearly ready boat for under 100,000. But recognize that at any price, you will still need certain things.
I would strongly caution against 30 to 35 ft. While many do it, including some on this thread (and they are certainly not regretting it), it is tight for
liveaboard. Very tight if you have guests. Our previous boat was 34, and while we absolutely loved her for weekend cruising while working for a living, a week aboard was about all we could take. 35 to 40 is the sweet spot in my mind for a
single hand
live aboard, and 38 to 45 for a double hand
liveaboard.