While I haven't pulled a significant amount of weight since I changed over to 37s I don't it's going to be as noticeable as you think. The H2 is just not designed to be a good hauler. If you don't expect much out of it, have some experience pulling trailers and are not worried about keeping up with traffic all of the time, it's fine.
I do have the programmer and that is the single best improvement short of turbo or supercharger one can do. You can really dial in the shifts relative to speed or RPM. The oddball shifts the stock tune had even in tow/haul mode makes you lose momentum too easily.
In deference to H2Rocks, (with stock tires) I have pulled around 10K lbs total weight about 145 miles with the H2 and 8K lbs over a 4 hour trip and never experienced a tranny overheating issue. And that was in the summer here where it's in the 90s during the day.
After everything I have found out over the last few weeks, if I wanted a mod just to make towing better on the H2, I would probably go the turbo route and that Squires System would be a consideration if I didn't take it on the trails.
Allen, anything that helps it breathe will be a good thing. My biggest issue between 35s and 37s would be stopping more so than anything else. That would be less of an issue if the trailer had electric brakes though.
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