What works best for you and your kayak? I use my WS Pamlico 120 for most my trips. I was thinking about getting an Osprey Kestrel 60L to put between my feet while I paddle, but figured I'd check here incase anyone can point me in a better direction? Obviously most Duluth packs are built for canoes. Does this make hiking packs more preferable for yakin?

Past trips I have used smaller sealine bags and have collected several so fit the gear to bags depending on the trip. At portages I have a larger Duluth type that I would toss things into. I have read others rig a rack and hang packs on. I usually strap a larger pack behind the cockpit holding sleeping pad, bag and lighter items. It can make a nice backrest and when light does not seem to effect stability.
At Canoecopia this year I made a point to take several packs to some of the boats I was interested in to see what I could put into the hatch. Rather disappointing. My 2 cents is see what you can get into your hatch and experiment a bit.

Yup, dry bags to go in the hatches, and then a large empty pack to toss the dry bags into for the portage. The more loose stuff you have, the more effort and time consumed at the portage.

I paddle an Ocean Kayak sit on top with a storage well in the back. My Cabelas Boundary Waters regular sized dry pack fits perfectly.

I use the Sealine Boundary 115. At first I took all my gear out and put it into the hatches when I paddled. But I decided to leave all my gear in my pack and strap it to the back deck of my yak. That ended up being the way to go! No fuddleing around on Portages, just unstrap the bag and go. I was worried the top heaviness would make the yak unstable. But it was fine. It will depend on what boat your paddling.

I strapped my back to the rear deck of my yak as well. It worked great but I was very careful to keep it centered. I did not have any real rough water on my trip although I think that I would have been fine. I am not sure that this would work with every kayak as my rear deck is large and flat.

I have tapered dry bags for the front and rear hatches. put the small stuff in these, and slide them into the hatches. pull them out and put one on each end of the paddle shaft and carry them through.

Large boundary bag behind the seat for anything else. Nothing on the decks.

I paddle a 17 foot necky Looksha IV

I use a Chesapeake 18 from CLC boats because that's what I built. The only portages I have taken it over is the Fall Lake set using a cart. But I've had it on Pine and Moose lakes as well.

Whatever gets you on the water and in the woods is great.

Aside from the portages, the kayaks offer a lot of advantages. You can paddle in wind or water that you can't take canoes in. You can also cover more ground with less energy exerted (although this is a bit boat specific).

Negatives are basically two. . .can't take as much gear as canoes, and harder to portage.

I have taken 17 foot touring kayaks, tandem kevlar canoes, and solo 17 foot canoe. Each has its merits.

If I want to take the dutch ovens and do a lot of cooking, the Wenonah Voyager comes. If we are going ultralight and covering ground. . .or big water. . the kayak.