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The ones I've played around with, have all gone up tubeless with the Bonty Charger instantly and stayed up for a solid few hours without any fluid at all. The set I had was doored badly. The bars snapped, the front wheel needed a minor true.
I'm no wheelsmith, but those with way more experience than mine seem to suggest so. Less dishing stresses on the spokes due to wider hub spacing. Shimano seems to think so at least. They've been pushing asymmetric for a while.
As for which rim, that really depends what tyre size you're going for. How wide are you going tyre wise? 22mm internal is great and gives a really well rounded profile on G-ones at 40psi.
Really tempting to try a 24mm internal with WTB's upcoming Byway tyre.
HG800 cassettes are awesome. Ultegra quality to boot. Really need to be double the price, but we haven't clocked on to the fact they're as nice and charge pittance for them.
I mean, realistically, you could have always gone for SRAM's offering in 34-36, but I do prefer them Shimano qualities.
If I had to go carbon, I'd just hit up lightbicycle really. Order rims, order Bitex hubs in any goddamned configuration that you can dream of (50g heavier than a DT 240's). Spend rest on CX rays and a decent builder to lace them properly for you. Sorted.