Something not mentioned is that sometimes the bigger boat you get, the more you have to work to pay for it which means less time on the boat.
What body of water have you picked out? 35' seems quite a specific request. Are you wanting a bigger boat with exploration being the excuse?
Or is that an ideal size for the body of water you've picked out?
Smaller, trailerable boats can give you a cabin with the bare necessities and be a little more nimble and beachable. Just food for thought. It may or may not fit what you're looking for.
Also getting a group of boats and going sailing is more fun.
I'm working on sail trim. It's an ongoing place of improvement. When I'm more comfortable in my skills, I may start looking into crewing in races (I don't want to race my own boat, lol!). It's a difficult thing for me to set the sails and not obsess over if they're working at maximum efficiency.
I'm not sure where you are location wise, but if you're still in Texas, lake Texoma has a bunch of "destinations", also lake Travis.
I do hear you on having destinations. I think there's a lot of fun in using your boat as a source of transportation. You may not be completely satisfied until you're on the coast.