Liveaboard Boat Choice
Dave, I like how you''ve thought thru the issue and, altho'' none of your questions have absolute answers, they show a thoughful approach to what will be major lifestyle change...so good for you. I also liked Gene''s answers (altho'' I will differ from them somewhat) and liked the practical real-world tone of his comments, which you need to hear.
I can''t/won''t answer your question about boat choice because no one really can. You need to shut down the computer, roll up your sleeves and spend lots of cold, boring hours prowling around in boats in order to develop a legitimate opinion on what suits you two best. (Fortunately, you live in an area of the country where day trips up/down I-95 make lots of boat shopping possible; imagine if you were in Dubuque). If you had more experience, the process would not take so long nor have some many unknown variables in it...but you''d still need to touch & feel, sit & stretch, take apart and explore lots of different boats before the trees will emerge from the forest and second- (third-, fourth-) order reasoning will kick in. If your experience is typical, you will ultimately end up making a different choice than you now expect, after looking at boats you didn''t initially know to choose from, and for reasons not now on your "must haves" list. Or you''ll buy out of ignorance and end up satisfied only if you are very lucky.
As for whatever level of experience you do or don''t have, it''s essentially irrelevant as it is what it is. Compensate for it with some clear thinking, a sustained research effort, and not a little tenacity and you''ll avoid at least the big mistakes, grow a lot from the experience and be the better for it.
Speaking of the big mistakes, buying big is a good one to mention. Liveaboard slips in the Annapolis area are hard to come by for folks absent independent wealth, and especially so for larger boats. (Annapolis used to be our nation''s capitol and, as such, is ''Olde''. Older slips are narrower, shorter and with fixed pilings...because that used to be enough to meet the need). Guest dockage on the ICW and in Florida isn''t cheap, either. Moreover, you intend to keep this boat for an extended period of time: Consider the accelerated costs of a larger, more systems-intensive boat, and reflect on how much accummulated expense that will cost you over time. As Gene mentioned, it''s generally more work to get a bigger boat underway than a smaller one. Finally, you are buying a boat to serve multiple purposes over the years, and for most of those intended years of ownership, owning, berthing, hauling out and maintaining a bigger boat just so you can do some daysailing seems like a real waste to me. At least logically speaking (tho'' logic of course fights to have its say in these matters...), doesn''t it make more sense to compromise on what you think you need for a few years and have a size boat that''s sensible for many more years?
I''d encourage you to take Gene''s observation as a challenge. Some folks who enjoy sailing AND choose to live aboard make it a priority to keep the boat ''sail-able'' and there''s no reason you can''t, too. That means different things to different sailors but to some degree that will mean less ''stuff'' being brought aboard, more daily/weekly effort at putting things away, customizing and modifying so the things that don''t have a home get one and, needless to say, constantly taking things OFF the boat, as well. (This is a battle I''m constantly fighting, and never feel I''m winning. But the victories, small tho'' they may be, at least make the rest of the stuff a bit more accessible). This ''keeping things ready to sail'' really does take relentless effort...while you may instead be picturing only the idyllic hours sailing without much concern for how you get those hours and/or what you do after they''ve ended. So - again - the issue depends on you and has no absolute answer. Also in contrast to Gene, we don''t generally find a need for more ''stuff'' when living aboard than when cruising, but that just reflects choices we make about our lifestyle. (However, this London winter makes a liar of me at the moment, with the dehumidifier and two heaters all posing trip hazards around the boat).
As for your other questions, inexperienced folks with bigger boats have to start a bit slower and work at it a bit harder, but two sailors should be able to handle a mid-40''s boat given the uses you describe. Larger boats will require more sail horsepower (aka: square feet) which require more handling effort, which these days is usually overcome with gizmos and extra hardware, which in turn adds a bit of expense...but unless the boat is overly heavy or overcanvassed, you will be able to find the hardware and develop the skills to handle any rig choice you make. (Keep in mind that one of the things that makes a given rig a good or bad choice is the rest of the boat; IOW there are ''bad'' cutters and ''good'' cutters. That''s why I don''t think there''s a simple answer to your ''rig preferece'' Q).
We lived aboard 3 winters in Annapolis, had a high-end diesel fired heating system, were eager for the adventure of it all (when the marina power would fail, we had more adventure than we wanted...) and found it a good experience, for us. Perhaps you two already have reason to believe the same might - or might not - be true for you?
Good luck on the adventure of it all; even shopping for boats is good fun!