You didn't mention your budget
, which is always an important consideration?
The trailering stipulation and "cruising" are diametrically opposed desires. Any boat that's big enough for comfortable cruising is one that's impractical to trailer every time you sail (unless it's just a few times a year, for seasonal storage
etc.). If you look into yacht clubs with moorings you'll find many of them are "working clubs" where the members do much of the seasonal maintenance
on a volunteer basis and they can be relatively economical.
I've owned a Dragonfly 920, 1000, and now sail a 1200. I originally bought the 920 for daysailing, and it was a good choice for that and weekending. But IMHO, anything less than 33 feet in a tri is "boat camping". The 1000 was much more roomy inside but still not enough room for a growing family
of 4. I'd have been better off and spent less money
if I'd skipped the trade-ups and started with the bigger boat. If your budget
allows, my advice would be to skip the baby steps and go for a bigger boat than you can trailer easily.