Is it worth it? Absolutely.
We towed our first boat (Freedom 170) back and forth for two years and couldn't wait to get a bigger boat and slip. Although it appears you have a tow vehicle which can clearly handle the task, I wouldn't even consider towing a 268 to and from the marina every weekend, regardless of how close it was.
You will appreciate it much more after you load up the vehicle (quickly

) with your supplies (clothing, food, etc.) and head to the marina for the weekend, and are sitting on the boat within minutes relaxing. Do this a few times and you won't look back.
As for painting the bottom, we boat on Lake Huron and most boats are painted (at least to the south where the water is a little warmer). I've had a couple of neighbours that didn't have bottom paint and when they pulled their boats in the fall, they had a hell of mess to contend with. We also looked at a couple of boats that were not bottom painted before we purchased our 258. To me, I saw the unpainted boats as an immediate added expense post-purchase. There's no way I'd pay a premium for an unpainted boat, unless I had a lift perhaps.
Our boat also has air conditioning. While we weren't specifically looking for this when we started shopping, we're really glad we ended up with it.
Enjoy your dock!