The others on this forum are much more experienced that I am, but here's my 2¢

1. In terms of making the hike easier, if you're overweight, losing a few pounds can help immensely. I include some high intensity interval training into my training regimen as well as weight training (compound, multi-joint movements).

I'm not sure what the 'dozen training climbs' are, but make sure your training includes some time at elevation.

If you're interested in heading out this way for training hikes, shoot me a PM with your email. I can include you on my email list for hikes. We have Whitney permits for the beginning of September. Between now and then, we'll try to hike at least once per month, most likely hike Baldy (via Bear Canyon), San Jacinto (tram), San Bernardino Peak and try to make it up north if possible (Langley area, White Mtn Peak, Mt Dana). This fall we'll probably try to do C2C again.

2A. I don't think you need a 4 season tent, unless you go in winter. You're tent looks good to me. There is a discussion on tents here. I just bought my tent a few minutes ago.

2B - I just bought one of those burners and used it at Chicken Spring Lake last weekend. It's not as fast as a Jet Boil, but it's tough to beat the price.

2C - clothing is something I struggle with as I have a hard time regulating temperature. This is what I used last weekend on my Cirque Peak hike:

Tops:
Champion Double Dry Competitor Compression Long Sleeve (instead of thermal top)
Champion Double Dry Men's Track Singlet (or something similar)

Jackets:
GoLite Demaree 800 Fill Down Jacket
Columbia Watertight Omni-Tech Jacket

Bottoms:
New Balance Men’s Sequence Pant
Running shorts
Sugoi Firewall 220 Tights
Trespass Qikpac Pants (waterproof)

The tights and waterproof pants stayed in my pack and I was able to do an ok job at regulating my temperature. On my Whitney trips (during warmer temps), I usually just wear my ExOfficio BugsAway Ziwa Convertible Pant and may bring rain pants as a precaution. I tend to run warmer than most of the people I hike with. On my first Whitney trip in August of 2011, I wore a tank top for a good portion of the hike. Some of the guys I hiked with started with winter coats/hats and never took them off.