one thing to keep in mind, is that if you don't see what you want in the REI store or online, they will order something for you so long as they carry that suppliers gear - canoe paddles for instance - they have small selection of Bending Branches paddles - but not the one's I like (Sun Shadow St - I have 2) so you could ask them to order them for you.

I generally don't always use dry bags, never canoe packs, but use some backpacks and duffle bags depending on the trip - just double or triple line them with trash bags - most backpacks will carry better than most dry bags, especially if the dry bag does not have a good padded hip belt.  If you do buy dry bags, get ones with good padded hip belts.

stoves -  I've hardly used my whit gas Coleman Peak1 stove since I have been using Jetboil stoves - convenient, clean and easy for me since all I do is boil water.  if you want to do a lot of "cooking" on your stove, then the Peak 1 is a good choice

a lot of gear choice depends on whether you want to go "deluxe" or "ultralight"  - 2 person tents are a bit tight, especially for two big guys, so a heavier 3 person
might be best - or not?  but I'd recommend a tent have two doors  (if a zipper blows out on you, you can duct tape it closed and still have a good access to keep the bugs out)  my current tent is the REI Quarter Dome 2P - you can get it in 2 or 3 person versions.  Either get a tent "footprint" or just a plastic (I use tyvek) sheet for a groundcloth to help protect the floor from abrasions

definitely a good tarp - REI selection is pretty poor.

good sleeping bags and pads are an essential - for almost all trips, a 30 deg bag is good enough - I always use Down bags (Marmot generally) packed so that there are at least two extra waterproof layers - never had them get wet on me.  once used a 40 deg bag - that wasn't warm enough for late May

sleeping pads, I like the Thermarest Prolite, and I use the 3/4 size self inflating ultralight ones, not the air mattresses

tent, stove, sleeping bag and pad, and packs are the main essentials - a tarp and good rain gear too - everything else is kind of optional and personal preference  I don't use a fancy cookset; solo, just use the Jetboil pot, tandem I'll take a small pot - just use little ziplock storage containers for bowls

keep weight in mind when you do your buying - keep a list and see what the weight accumulates to - that will tell you if you really want those extras, or to go with the lighter versions of gear