1) The final 400 feet is a challenge but do able. When I did it the snow was deep and soft and we took the most direct route. The hardest part was right at the begining was rocks covered with ice, I used my axe as an ice tool, and front pointed up this section.
2) We didn't bring rope, but when the other team that summited with us pulled out their rope, we asked if we could rap down with them.
http://www.youtube.com/watch?v=ASthZZJoBIA3) I personally wouldn't mess with trying to go down the main route, but self arrest skills are necessary. (as seen later in the video above) My first attempt at Whitney in April was postponed because of a fall from someone descending at night and unable to arrest. Sadly, I helped with the recovery.
4)Bring a map, and know how to use it. If the weather has been good you'll have to problem following the route. If you're the first ones after a storm, you'll be rebuilding the route. If you're familiar with the area then the major landmarks are easy to spot.
My normal schedule for all my sierra climbs no matter the season is leave work in Reno on Friday and head straight to the trailhead (in this case the portal). My preference is to make it to iceberg on Saturday, then Sunday the plan is to summit take a quick nap in camp, then hike out, pizza in Lone Pine and a drive back to Reno with naps along the way to be back at work on Monday morning.
My suggestion is that you should at least make it to Upper Boy Scout that first day. Oh and have fun!
Edit:
Oh.. BTW, this is a trip that I love doing every year before permit season! It's probably about the same difficulty, physically, as Rainier (depending on conditions) except you don't have to worry about crevasses or bergschrunds. The snow makes the area beautiful and interesting. Temperature swings are extreme especially if the Sierra is expereincing it's normal June-uary. Hot clear days with the sun beating down followed by very cold clear nights.
