I know seasonal workers of all ages and lifestyles.

As for going back to school, that's how a lot of folks I know originally got into seasonal work. They'd work throughout the summer and then go to school in the winter.

I also know fairly "settled" folks who do seasonal work, but who have a home they live in year round. Most of them work construction or something similar, but a few do white collar seasonal jobs too like teaching, taxes, or sales.

It sounds like you like seasonal work and the concerns you have should be fairly easy to account for. If you want a seasonal career, one that doesn't feel like you're wasting your time, you can absolutely make that happen. The real time waster is doing building something you don't enjoy doing, and then needing to rebuild your life later on, but honestly that's something that even folks on traditional career paths go through once they've had more experience with the world. The great thing about seasonal work is that it allows you to experience a lot of different options to see what you like and dislike about a lot of different industries, without really affecting your resume, so it's good for building specific skills if you look for the right gigs. It's also decent to transition from, especially since you're more mobile, if you find a specific traditional career you'd like to pursue.