Pickle, I had 04 Outback and switched to 06 LSV in September..
LOVE IT...
I sold mine outright and bought a used one. Great condition.
I have no experience with Trades on boats, but suspect you could come out a little better on an outright sell.. Around here, right before Memorial Day is the best time to sell one! I had several staked out when I sold mine so I had a couple of options so I was only without a boat for 1 weekend.
I love the space, storage, wake, built in Grav III ballast, etc of my LSV.
Use the boat builder function on here to get an idea of MSRP of one optioned like you like it.. .not sure how much dealers will knock off, but expect around $40k+ with Grav III, wakeplate, stereo, cover, etc..