Neighborly Experience
Lance, there is a wealth of wisdom in the prior responses. From just up the road, let me say that having owned/sailed in everything from an 18' trailerable to our current 34 footer, I've learned and had different experiences with each of them. We outgrew the trailerable pretty quickly and a larger boat allowed more coastal exploring. However, I miss being able to sail some of our larger inland lakes. It, like most things in boating, is a trade off. I DON'T miss traffic jams at boat ramps or the pain of stepping/unstepping the mast for my weekend sails. I know there are hundreds of places to explore in your/out back yard (the salt water one)and a small boat would be plenty good to do that with while you're figuring out how sailing fits with your life and developing some basic sailing skills. The local chapter of the U.S.Power Squadron has course offerings; I'd also taken a course over at SMTC/SMCC years ago. One of the posts made note of not scaring the *&#! out of your 1st mate or otherwise subjecting her to unreasonable hardships of sailing. Have that engraved somewhere. In this regard, bigger is better, safer, more comfortable, and in short, comes closer to mimicking a travel camper vs a tent. It's a matter of what you (two) are likely to be comfortable with in all regards. Lastly, if you'd like an opportunity to enjoy the pleasures of spring commissioning on a bigger boat, let me know--the snow should be gone in another 4-6 weeks! But really, if there's anything I can do to help as you move along this process, plese feel free to e/m at your convenience.