Erik's right. A decent installation of vinyl will show no defects like sagging. Even a half-arsed install will look great for 20 years...it takes 1/4 arse or less before it starts to suck.
Those insulated sidings are probably very expensive. It would be cheaper to use multiple layers of the foil-faced 3/8" styrofoam insulation that is normally put behind plain old vinyl. Unlike the thicker, larger sheets described above, you can stagger the layers to avoid cracks more easily than caulking so many joints. Either way, you could put an additional layer of vapor barrier (Tyvek / etc) on the outside of the insulation. Your contractor and neighbors will think you're 100% crazy.
For vinyl that looks nicer, look at the premium varieties that are shaped like shingles instead of clapboard. They come in thicker, stiffer, taller, less-long pieces that interlock on all four edges.
In the past, when doing a vinyl siding job, it was common to wrap the trim boards with sheet aluminum. Now it's starting to become common to replace trim with plastic lumber. I like that stuff, and it's probably right for you -- you would not like how easily dented the aluminum is.
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