Welcome to WhitneyZone, Matt. I hope you and your friends find lots of helpful information here.
Unfortunately, Inyo N.F. does not allow permits to be traded or sold -- the person named on the reservation is the only one (or the alternate leader) who can pick up the permit at the Visitor Center. This policy prevents hackers and scalpers dealing in permits like they did Half Dome permits last year.
As for your mid June date, this year might be ok. The Sierra has had a near record dry winter this year, so the trail will clear much earlier than normal.
Last year, the switchbacks were finally usable July 11. In 2010 it was July 1. But those were heavy snowfall years. Looking back at
snowfall records, 2007 is more representative of this year. Looking up a report on wpsmb, I found
this posted 6-3-2007:
I was up there on Saturday June 2 for a day hike and the conditions were excellent. It is hard to believe the difference a year makes in the snow pack. There is very little snow on the trail and that is only on the switchbacks and a few spots above trail crest. The only area of concern to proceed with caution is at the cables. There is still snow and just a small area of rock along the cables and early in the morning it is covered with ice. It was passable but required careful steps and holds. I would not consider taking an ice axe and crampon unless you are going to go up or down the chute. There is still snow there but it is melting fast. A good report to look at is Bob R's "Mt Whitney Trail 23-24 May" post. Click on the pictures link and find the photo on the first page of the cables, although more snow has melted it is still pretty representative of the cable section. Good luck and have fun, it was a beautiful Saturday on top and very few people on the trail.
And Bob R's pictures are here:
2007-05-23 Whitney, Muir, etc. Look at the pictures starting especially at "38 Trail Camp", and remember that these are a few weeks before you are going, and this year is probably even less snow.
