Jason,
I'll just add to what Bob said.
In my opinion, there are three highlights to the loop, and two of them aren't officially on it: 1. Rae Lakes, 2. Sixty Lake Basin, and 3. East Lake and Lake Reflection.
I did this loop last year with my 62 year old dad. It was his first time backpacking in the Sierra, and his first time backpacking in 30 years. We did a 4 day/3 night loop with the following itinerary:
1. Start late on the first day, hike to Upper Paradise Valley (Bob is right–there was a domesticated bear here)
2. Hiked past Rae Lakes, into Sixty Lake Basin. Something like a 16-17 mile day.
3. Hiked back into Rae Lakes, over Glen Pass, started the descent of Bubb's creek, then hiked up to East Lake. East Lake had an entire troop of boy scouts and about as many climbers, so we hung out for a while, then hiked back down to Junction Meadow and camped there.
4. Hike out. Quick and easy. Only a few hours from the TH.
That's probably the itinerary I'd recommend, although if you have a full first day available for hiking, you might go all the way to Wood's Creek crossing. That would be about 15.4 miles, with a few thousand feet of climbing. You could spend more time lazing about in Rae Lakes and Sixty Lake basin on the second day, in that case, or dayhike into Sixty Lake Basin and camp back at Rae Lakes on the second day. Also–obviously–if you have it in you, head up to Lake Reflection and camp there, or stay at East Lake and camp there, on the third night.
The spur trails into Sixty Lake Basin and up to East Lake could also be done as dayhikes, if some of your group feels up to it, and others don't.