I can finally feel my toes again after my last trek, so I guess that means it's time to plan the next one! I've been looking at the Four Pass Loop 10mi southwest of Aspen, CO, but I've stumped Google with a few questions during my planning; so I humbly ask ya'll for your opinions...

-Is there a particularly good time to hike this area? I've seen trip reports from around July to September. I'd like to go sooner rather than later, but I haven't heard if the passes are...passable as early as May.

-Can the trip be done with a hammock? I think the trail drops below the tree-line often enough for a 3 night trip over the 25mi length of the trail, but I've been unable to find if they are close enough or sturdy enough to use. I'm hoping "yes", since hammocks are awesomer, and I need an excuse to make an underquilt and top quilt

-The passes are all well north of 12,000ft. Well beyond any hiking I've done previously (~9000ft). Is there any legit way to prepare for the altitude, or is it best to simply get in the best shape possible, then acclimate for a day or two prior to embarking, and take the trails slow 'n steady? I do plan to do at least a couple 20+ mile multi-day shakedown hikes, but at Texan altitudes (<8000ft)

-Any special gear I should consider bringing aside from very cold/wet weather gear & shelter? I suppose I'll have to get a more expensive cooking device than my alchohol soda-can stove for the altitude/temperatures out there

-Is there anything particularly cool (but not super-expensive) in Aspen or the surrounding area I should be sure to check out after I'm done adventuring? I just know Googling "cool stuff in Aspen" would take a few lifetimes to sift through

This expedition doesn't seem quite as cut-and-dry as the Napali Coast trail, and I really appreciate the advice