Hi.

Couple comments.

No way I'd drag a sled. Just shoeing is hard enough.
I love the MSR Lightning shoes although don't have the
"ascent" option. Highly recommend them, although I
also recommend you get a spare pin or two to take along
(I lost a pin on a trip once... and had to use cord
to fix the shoe so it didn't move at all)
MSR said it happened rarely... although I think they now
sell a kit so you can read what you want into that...

Grew up in GB... graduated from UW Madison... smile
But I know what I got here w/Yose and the Sierra... not
going back to Wisconsin (knock on granite).

With that many miles I'd start Mid-May to have a chance
of being able to walk w/o the shoes.
Good Luck