Congratulations on winning your lottery ticket. Only 1 out of 3 or 4 people win a reservation.
Based on your (in)experience, you want the Main Mt Whitney Trail, JM35. The other, JM34, is the non-trail North Fork of Lone Pine Creek, sometimes called the Mountaineers Route. It is steep, rugged, and not a trail in some places. The JM35 is the regular Mt Whitney Trail, a well-marked trail (unless it is covered in snow, as it is in May and early June.)
Mountain guides are available, but they take people up the Mountaineers Route, and their clients are outside of the lottery process.
A private guide or even a knowledgeable friend would need to have the same permit as you, so that isn't much of an option. Note that you won't be alone on the trail, as there are 160 permits a day to hike that trail. People often start alone, and then make friends with others on the trail.
If you want to be successful, here's some advice:
* Learn as much as you can about the Mt Whitney day hike. There are a number of good books on it.
* Learn about Altitude Sickness (AMS). Plan on going a couple of days early, and staying high: Horseshoe meadows, Onion Valley, even Mammoth Mtn Inn at 9000' elevation. Sleeping two nights at 8-10k elevation before you hike will help greatly.
* Do some practice climbs: Mt Dana at Tioga Pass in Yosemite is good for SF-area people. Long trail hikes in Yosemite are good -- Panorama Loop, or Clouds Rest.
* If you can, visit Mt Whitney on a weekend this summer. Climb to Lone Pine Lake and back -- no permit required for that first section. Being familiar with that part of the trail would be helpful, if you start hiking before daylight on your Big Hike.
Good Luck!
