Thank you for those replies.
And please forgive me for knowing too little to even pose a proper question...
My own experience level is somewhere between nil and novice. I have a basic knowledge of seamanship.
My main reason for finding and joining this site is to learn, which I really do best by observation, and by interaction with those who possess expertise. I am in the right place for that, I think.
I just want to be as prepared as possible.
I would like to live aboard her full time. Probably out of the Gulf Coast of southern Florida. I do have one eye on the Keys, also.
I would like to be able to sail some distances, though, and to cruise for as long as a week. And I definitely must be able to single-hand her.
My budget for this is yet indefinite, but it certainly won't be unlimited. Nothing too extravagant. I'll likely be looking for a good bargain.
Chrisncate: I'm sorry, but I do not understand. Why would you say that the question of ketch or not is not an issue at 30'?
Again, thanks, good people.
Captainmeme summed the ketch issue up very well, 30' is small for a ketch with not much (if any) benefit. Just more to deal with.
You seem to be on the right track so far, keep in mind that as you learn your needs/desires will change - so it's a good idea to get something that you think will suit your needs now, while still keeping an eye on re-sale and moving on/up in the probably nearish future.
If asked, I say keep it cheap and maybe bare bones initially - solid sails and rigging, a livable interior, a decent motor (ahem, cough cough..), acceptable ground tackle. Have a go at it and just see how things progress and learn what suits you. Getting caught up in finding the "just right" boat when you just don't know yet, might lead to getting locked in on something you find you don't really want. Also I'd highly recommend finding something that you don't have to get into a bunch of refitting projects on. Refitting can take up so much of your life and time the entire dream can slip away on you (ask me how I know).
Best of luck, please keep the forum posted on your progress!