Waiting kills the dream. Do it as soon as possible.
Listening to conventional wisdom kills the dream. You can
go outside the box and there are still many innovations to be found. Cruising may be old hat, but refitting/outfitting boats is still wide open and doctrine in this area is nothing to be taken too seriously imo.
Not realizing/accepting that you will need to refit your own boat from top to bottom can kill the dream. Be prepared to work very hard unless you hold the mega millions ticket.
Biting off more than you can chew with a too big boat kills the dream. Go as small as you can stand. 30' is enough for sure.
If you really want it, it's something you realize is a life commitment unless rich - it becomes what you do
Everyone does it just a bit differently, you either find your niche or you accept that you don't need to necessarily devote your life to this and just sail when you can, and live on land. There is no shame in day-sailing.
We gave up everything to pursue an obsession, and it does have a cost - be aware. We personally are at the end of the major full refit (so much in that sentence, it's so easy to type but so hard to convey what it means in reality) and all I can say at this point is that I am glad we did it this way - I know every flaw, every bolt on my boat and I feel that I am really ready to take her out there now. I have come to believe that those who chose the DIY route have the best chance, maybe even equal/better to those with the checkbook.
Bear in mind my opinion stems from the perspective of (making a boat for) cruising rather than living aboard. So... Imo, yes - you can do it (young and not rich), it is worth it, and it's awesome. Go for it! I personally like a full keel with a cutaway forefoot, narrow beam, low freeboard and smallish cockpit. I like sexy old boats in the classic sense, like folk boats (that style) for example..
Check out Wind and Tide by Jay Fitzgerald for info and inspiration. It's not on most cruisers list of required reading, and he is borish when he gets all philosophical (who isn't though?), but it should be on every younger potential cruisers required reading list imo. Best of luck, and fair winds