Smallish cruiser w/ resellability
Tad, that''s a great question and I''ll bet we''ll see a lot of boats nominated. But here are some related thoughts to help round out your considerations:
1. Where on the East Coast? There''s a significant difference in the sailing and cruising venues of e.g. Long Island Sound or lower New England, the Chesapeake, the Carolina Sounds, or FL''s Space Coast. Knowing were you''ll be homeporting the boat is quite important for several reasons. Obviously, your home waters will affect the kind of sailing and preliminary cruising you''ll do, the range of weather conditions you''ll need to face, and how significant draft will be for you. Stating this will help you get better suggestions. But another reason is that...
2. Given your plan to purchase a ''learner boat'' and trade up if the Grand Plan remains in place, you will be better off purchasing a boat well known in your home waters, for which there is a sustained demand because it suits that locale and is held in high regard. I hope you are or will consider working with a good local broker because this is one area where their in-depth view of the market can be especially helpful. (Choosing a ''good'' broker is a topic that''s been discussed here before; you might search the archives).
3. When shopping with a $30K budget, you''ll find yourself straddling multiple continuums (continua?): older and perhaps in more need of repair or cosmetic upgrade but also larger vs. newer and more ''turn key'' but smaller; more systems and gizmos but smaller for a given price vs. simplier boat with fewer amenities but perhaps a bit bigger for the same price; better build quality but smaller due to the cost of quality vs. ''pedestrian'' build quality but a bit bigger for the same cost. Give some thought to where you want to be WRT such variables; those are questions you need to sort thru vs. just accepting the opinions of others.
4. Don''t be too quick to avoid some amenities, as you seem inclined to do, as in your Grand Plan you''re going to be using the boat as a long-term home, not just a magic carpet, and so comfort and things that make life easier will be welcomed. (Cruising can in reality be tough work in at times pretty trying conditions; a few comforts help offset this). And guess who needs to understand and know how to fix those amenities? Your ''learner'' boat, if it serves its purpose, will in part be teaching you how to maintain, repair and upgrade systems. So...e.g., a diesel engine, pressure & hot water system, a decent self-steering system to help with that single-handing, a jib furling system...these are all ''extras'' that will serve you well when learning, and ultimately with the big boat. The same logic argues in favor of preferring a somewhat larger boat over a smaller one as our interim choice - imagine how you''ll feel when thinking of stepping up to a 38 footer from a 26'' vs. a 31'' LOA boat. (Also, don''t do what I just did for purposes of simplification: think ''displacement'' when thinking size, as it will more typically predict cost, volume and - when also considering length - performance).
5. There really isn''t any facet of sailing, living aboard for periods of time, cruising, navigating and much more that you won''t be eager to learn about. In such cases, owning a boat with a local, active owners'' association that has rallies, a seasonal cruising program, kids activities, etc. can be a short cut to this learning and provide a structural envelope in which you can achieve your skill building. This can also be true of a local yacht club, sailing club or marina. Owners'' associations also can offer a huge wealth of (usually, on-line) reference info when attempting to learn about systems, how to make upgrades, source parts and such. You might just want to keep this in mind a bit when picking your boat.
There are many, many boats in your price range that will allow you do what you wish re: sailing, assuming it''s structurally sound, safely navigated and thoughtfully sailed. Thus, I don''t think there''s one or two ''right choices''...and therefore mentioning of some other criteria to consider. Good luck on the hunt!