My 42' sloop has a high freeboard, too. I have an 85lb yellow lab. His name is Max, and here he is on watch:
http://wdsg.com/gallery/main.php?g2_...geViewsIndex=1
Some years ago, I built a nice sling for him which worked with the main halyard/electric winch. It worked, but was a pain-in-the-butt, and he never really liked it.
One morning, anchored in a very foggy Maine cove, I was standing in my inflatable, which I'd toweled off. Max was on deck, waiting expectantly for his run ashore (he absolutely won't go on the deck, so we're stuck with several trips ashore each day).
I was contemplating whether to rig the sling or not, when out of the fog came an elegant white haired lady rowing her skiff. Last evening, I'd seen her and her mate enter the anchorage and come to anchor near me -- all under sail. Very nice.
Noticing my indecision she asked, "Why don't you just ask him to jump?"
And so I did. And so he did. Very nicely, thank you, lightly onto the tube of my Caribe RIB, then up to his station at the bow where he likes to ride, and where I'd already laid out the towel for him. Very, very easy.
On the way back to the boat I was wondering about getting him back aboard. In the event, it was no problem. I simply tied the dingy alongside, then hoisted him up until he got his footing on deck.
Sometimes the easy way is best :-)
Bill