Hi Kelsey. First welcome to the forum. Hope you change that “very novice sailor” condition into “Yes we sail.. we are learning a lot... but we enjoy the water and can sail safely”.
I am that “John” that Meriachee mentioned. I located my boat up on the Puget Sound and drive 250 miles one way to spend time on my boat. This is a new boat to me and very different from my trailerable 15ft Montgomery I had for 19 years.
The 15ft’r was a back pack tent on the water. It could sleep two close friends and there was space in the cockpit to have “a Kitchen, Lounging, and showering” space for one at a time, or I could use it to sleep out under the stars. We sailed on rivers, lakes, and the Puget Sound. She was a great “little” boat. 750lbs on the trailer. I could pull her with my 1989 Vanagon. Not much on comfort, A terrific sailing boat, versatile, and gave me wonderful adventures.
But I wanted more. Enter into my life the S/V Hadley. She is 35 feet. Beds for 5, Kitchen, Head, Engine, able to sail in adventuresome waters that may not play nice. But she is 5 hours - 250 miles from my home. She needs a lot of work (born 1974 about 12 years of neglected maintenance by previous owners). But she is beautiful. And we have started to have some great experiences.
The challenge I see having a larger boat, say a 6 to 9 meter boat is the time/cost you spend on maintenance and mooring vs sailing. Especially if you enjoy backpacking and you just want to take these skills on the water. In that case I would lean to a trailer boat 4.6 to 5.5 meter boat that is designed to pull behind a car. The other boats can be put on a trailer (trailerable) but there can be a lot involved.
Beyond 9 meters you are going to want the boat in the water all the time. The Salish Sea waters are great for that type of boat. Additionally you experience winter weather that is harsh on boats in the water. So you need to store the boat. This would be best, in my opinion, right at home. My 15ft’r spent the winters next to the house under a tarp. And on those special weeks when the winter weather was mild it was nothing to go for a day sail. Rigging took only 30 minutes and I was on the water. Pulling her out and prepping her for the next adventure was less than 90 minutes.
There are a number of boats in the trailer category. Sage manufacturing in Colorado makes a great boat.
I wish you best in your search.