It can certainly be hard waiting, but in the long run, you'll be better off waiting until you can afford something bigger. A little self-discipline now, could save you from making a rash decision that you regret later.
Very true. Boat mortgages are stupidly expensive, and you already have
a boat. Also, you will never make back on an old 30 footer what you paid for it, even if you do $10K of improvements, half of which are just to combat age-related problems.
Enjoy what you have, and maybe challenge yourself by racing it or going out in heavier weather than you are used to. A smaller boat is a better teacher in some ways.
The only other way to do this...maybe...is to partner up with someone similar, and then you'll just need half the purchase price.
The latest Practical Sailor compares the Pearson 30, the Triton 30 and the Catalina 30 as affordable "classic plastics". Even though I've been aboard Pearson and Catalina 30s, I think the Triton is the best boat, but that's because I'm focused on "all-weather sailing" and generally classic construction. Round-the-buoys racing and drinks in the cockpit? The Catalina 30 (the C&C 30 is even better, IMO). Weekend cruising? The Catalina 30 or the Pearson. Liveaboard with extended cruising? The Triton.
See how that works? There is no one answer. Eventually, you'll find a number of "good enough" boats that avoid the "wrong answers", but have subtle differences that will determine which is best for you.