dave...my suggestion is to demo both kayaks and then choose.
If you choose a new Outback, upgrade to turbo fins and the sailing rudder before you leave the dealer.
Regardless of which kayak you choose, as a minimum, count on adding a fish finder/gps, Hobie FF battery kit, safety flag with light, anchor, PFD/life vest, tow line, 2 rod holders, maybe the anchor trolly and a carrying cart for the Outback......I launch straight off my trailer.
For me, I went from a 2010 Outback to a 2013 PA-14 because it has more interior room and the seat is more comfortable if you fish for more than 4 hours at one sitting.
Additionally, I am over 70 and the ease to turn around in the PA-14 is much easier for me.....even accessing something out of the front hatch is easier.
Stability wise, either kayak was a no-issue......the PA-14 is heavier, but I already owned a Hobie Trailex trailer.....unless you have a truck, car-topping the PA-14 can be done, but takes an investment in loading equipment to ease the task......a gook Yakima carrier setup and loader is almost the same cost as the Trailex trailer...and car-topping on a windy day can be dangerous to your health!
I fish both local lakes and the Columbia River and love my PA-14!