Interestingly, we've talked about whether we would sell our M-15 (much like your Compac-16) and as you have pointed out, we've concluded we would miss the ability to trailer to mountain lakes. I've also started looking a little bigger than 20-25 and wondering if I should scratch trailerability off the list :-)
I would! Even trailering a 23 and trying to rig it, and mostly launch and recover it taught us that as far as a trailer sailer that less is more. We absolutely love the size of the 31. Shoal draft yet built to cross oceans and sea kindly plus seaworthy.
I noticed you are in the Shenandoah Valley. We live outside of Charlottesville. This weekend there is a gathering of the small sailing club at our marina on Saturday. I do know a fellow that is bringing his Flicka and joining us. Maybe you should consider a road trip for Saturday! You can see a Flicka and a 31 and compare. They allow non-members to attend for a $5 contribution for the grill and beverages. Folks are encouraged to bring sides. It is a Cheeseburger in Paradise theme so tacky flowered shirts i am sure will be visible! There are also several Compac owners coming from other locations and joining in.
Hey why not! Reach out if interested and I will provide particulars. Oh, there is a 23D at our marina as well.