I just spoke with the very helpful Jesse at Viair. I'll try to write down the details, although there were a lot (whew).
So, if you look at the chart I posted above, you see that the "RV" compressors don't necessarily fit for us (although of course they would work fine, I've used my buddy's 450P-RV and it's great). But, it will go up to 150psi and have a 100% duty cycle at 100 psi. It also has 60' of hose (plus 8' of electrical cord). So kind of overkill. I have thus temporarily ruled them out.
If you look in the next column to the left, it's for people who want to "air up or down" for going off-road. I might like to start trying this. Not sure if I will but I'd like the capability. You can see that those are all battery hookup ones (alligator clips), and even the smallest of those, the 300P, will work for a 33" tire (stock tires on the Chinook are just under 30" diameter).
The next choice is about Automatic or not. They are plusses and minuses to each. Basically, in order to check the air in the tire as you are filling, you have to cut off the flow of compressor air. On the non-automatic one like the 300P, that means you walk over to the compressor, shut it off, then back to the tire to look at the inline gauge. So right now you are thinking Automatic for sure, right? BUT, on the Automatic you have to hold it on all the time you are filling, like a gas pump where they have removed those little holder-onners. But when you let go of the trigger the compressor stays on (but kind of like in neutral so no air is flowing) and you can check the air pressure right there. With the non-Automatic you don't have to hold the trigger while it fills. The 300P is not Automatic. I think you have to go to the 400P or above to get that.
There are at least three different chuck types available (not all on all models). The 450P-RV and the 300P both have the one where you put it on and then flip a lever down. I know some of the smaller ones (77P vs. 78P for example) have either a screw on or the flip down. And there is a reverse chuck they mention (like to use on duallies that have short stems), but I'm not sure which model(s) that is on.
I then asked about someone who only wants to use it in the "normal" way to add air to a low tire. Then the 87P or 90P could be fine. They don't have thermal cutoff, and the gauge is on the compressor not on the hose at the tire.
So I'm still not sure which one I want! I'll have to compare prices, but I'm thinking maybe the 300P if I don't want the Automatic function (not sure I do). I'll have to look at my buddy's compressor again because I don't remember having to hold the compressor air flow on, so maybe that's no big deal (or maybe I even misunderstood).
If you narrow it down to two or three models you can look them up on Amazon or wherever and compare more details.
By the way, they said that the duty cycle is basically linear. So, for example, if a compressor had a 33% duty cycle at 100 psi, it would have a 66% duty cycle at 50 psi. Since many of them are rated at much higher psi than we would typically use with stockish tires, that may come into play in choosing. The 300P and up have a thermal cutoff.
Hopefully this doesn't muddy the waters even more. I'm still not out of the woods in terms of completely understanding the nine billion choices
BG