So I know that I've been doing a lot of talking about motorcycles lately...but it's been on my mind.
Right now I'm leaning on maybe trying to save some coin up to get an "older" sport touring type of bike. I'd probably try to keep the 250 around, but use the bigger bike for touring with Cathy. Something like a Kawasaki Concours ZG1000 would be nice. They are virtually identical for nearly 15 years, so you can find older examples in great shape for pretty low prices.
You can get a new-ish one for less than $4k. You can get one from the early 90s for around $2k. Good thing about them is they are generally bikes that were owned by "mature" individuals so they are usually well taken care of.
It seems like they would be a viable option for what I'm looking for.