I can't speak to the Chevy/GM specifically, but as far as the van goes...
I bought a 22 Cruiser last spring (congrats on your new boat!). I didn't have a vehicle that would tow it, so I went through the same "what should I buy" process. I ended up with a late 90's Ford 3/4 ton camper van with a 5.4 V8 (gasoline). To start my towing experience, I picked up my boat and towed it 4,000 miles (including mountain passes)

I thought it towed pretty well, and the van felt capable. Mine is a 3/4 ton HD, so this may be different if the 1500 is a half ton; but with the van loaded up and the boat/trailer on the hitch it did not cause the rear of the van to sag.
My particular van has a 13,000# GCWR*. Loaded for bear (with driver), I drove it to a scale and it weighed in at ~7,400# -- so that leaves me with 5,600# (I also made sure the rear axle rating was not exceeded, although I forget the figures). I have not weighed the boat separately yet, but I knew I was towing it "light" on the way out. It's on a 5,200# GWR trailer, so I need to stay below that anyway (and I think I can do that without duress). So a note is that I would check not only the "towing capacity," but really do the math/weighing to see where you come out with the GCWR and the RAWR* with the van loaded as you normally would like it to be. As an example, my van is rated to tow 7,500 lbs.
However, since it weighs 7,400# when I have it loaded for travel, and since the GCWR is 13,000#, well that adds up to 14,900# so it does not leave me the "rated" 7,500 for towing. I couldn't tow the full 7,500# tow rating unless I really emptied out the van (probably of seats, driver, and upholstery!). I did similar math with the rear-axle weight. You can see that going just by "tow rating" might leave you with a surprise (or might not, but it's good to know).
I really like the van for a traveling platform. I had considered a pickup or SUV - both of which could be very nice - but I really do take advantage of the van on road trips (with and without boat). I don't feel underpowered at all with the 5.4, but then I'm used to "finessing" it with a 4-cylinder car. I did downshift going up the big mountain passes, but I wasn't crawling by any means. A bonus is that I average 16mpg on the road when not towing, which I wouldn't be able to do with the V-10 (gas). The wheelbase is reasonably long, at ~138", which, as I understand it, contributes to steady towing.
Recently I had a chance to tow a similar boat with a Ford F-350 4-door dualie with a V-10, and yep.... barely knew it was back there :smiled That said, for my particular traveling, I prefer the van/V8. Like boats, it's all a matter of compromises/choices. One thing that I have found super useful: I bought a Scan Gauge II (engine just needs to be new enough to have OBD II), which was around ~$140. This gives me lots of detailed information that I didn't have without it. Just a few examples:
Engine RPM (I have no tach)
Engine/coolant temperature (in exact degrees)
Transmission fluid temperature (in degrees)
Specific and average MPG
Percent of available engine load
I'm not a patient tech person, but even on the road I had it up and running in about ten minutes (basically plug-and-play). Gave me great peace of mind. What I really wanted was the Transmission fluid temperature, but the other data is nice too.
One more note: I put new disc brakes on all four trailer wheels. They are hydraulic/surge brakes. I think the van now stops better when towing than when not - really a confidence booster. I considered going electric-over-hydraulic, but didn't because the shop (in a FLAT area) had no experience with them. I was a little bit concerned about the surge brakes in the mountains, as I had read that if you brake going downhill, then releasing the brakes can be a problem (which makes sense). In practice I found that I could select a gear on the transmission (an automatic, normally) that would allow me to go down 6% grades without really touching the brakes (maybe a couple of minor taps). I didn't have any grades steeper than that, nor did I have snow/ice. Based on that I'm no longer in a rush to convert to E-O-H brakes.
I do think that pickup trucks are slightly more pleasant to drive - maybe it's the steering or ...?. That said, I'm happy to trade that for the van features, at least in my current mode of operation (just got back from a non-boat trip - so nice to have "home" along with me

).
Another consideration is whether you plan to tow at either end (or the middle) of the continuum. i.e. Long distance, mountains, fully loaded cruising boat/van vs. short, occasional tows on flat terrain with a day-trip loaded boat.
Sunbeam
*GCWR = Gross combined weight rating, i.e. van, contents, boat, and trailer can weight this much.
*RAWR = Rear axle weight rating. The limit of weight you can put on the rear axle (which you can weigh at a scale). (Comprised of whatever weight is on the rear axle of your loaded van, plus the trailer tongue weight (give or take).)