If your shoulder is really limiting, you might want to consider trailering. I took out a Yugo with a 650 Yamaha motorbike, had to put the Yugo on a flat bed, couldn't tow it, so I understand bad shoulder. (thank God it was a Yugo, or I would still be dead!)
I tried Yakima Hully rollers, but my rig was way too high.
I could not find any cartop loader that would lift anything heavier than around 40 pounds or so.
I bought a cheap little trailer from an outfit called Harbor Freight
http://www.harborfreight.com/870-lb-cap ... 42708.htmlThe trailer's assembly manual refers to an add on boat kit, which extends the tongue and has a set of v brackets, should hold your Outback nicely, altogether under $250.
MUCH easier to load. I started with an Adventure Island, now have a Tandem, might have to get a bigger trailer, but built an extension to support the Tandem out of scrap wood. It is not galvanized, so I do not submerge it, just back to the water edge and slide in or out. Use a small ratchet pulley to help haul it on. Have also just used the beach cart to roll the boat to the trailer. The whole thing fits into my toyhauler RV trailer.