Hey there, welcome to the forum
I'm new here too, and in largely the same situation as you. Bought my first boat fairly recently (1968 25 ft Seafarer Rhodes Meridian) and have been sailing the Indian River in FL ever since (and loving it!). I've also started thinking about a bigger boat, but I was a bit more tempted by the bigger end of the spectrum, maybe up into the low 40' range (tayana 37, westsail 42, freedom 40, valiant 40). I worry about messing with a good thing though... As it stands I can leave the slip, sail for 2-3 hours, and clean up in 20 minutes and be done. As a result, I'm logging a sail every couple of days. I'm guessing you are in a similar situation with your 24 - quick and easy. A bigger boat brings the promise of longer trips with more family members (My boat is great for two, but three's starting to be a crowd). However, I am a bit nervous about scaling up and making sailing more of a chore... right now it is easy and fun. That said, I'll probably get a bigger boat in a few years. Do you have any similar apprehensions about a bigger boat?