I use the same shoes, only the non GTX version, and can generally hike around 20 miles before I get “tired feet”. I used a pair of Inov-8’s, that so many people like, and my feet were “tired” after only about 14 miles. What it amounts too is that everyone’s feet are different. It could have been the fire road, but maybe not. Insoles might help, but which ones will work for you is hard to say. You shouldn’t need to break them in, that is for big heavy boots. You best bet is to go to a running store that really knows what they are doing and have them fit you for trail runners. No offense to REI, but every time I go in there, I am less than impressed by the knowledge of most of their staff.
You do really need help with your big three, and you already have some good advice so I am going to echo much of what they have said.
I would sell your tent, bag, pad, and pack and use that money to start over. You can get some good deals online sometimes, but the gear swap here, might be your best bet. For Example :
Shelter: John Divitt is selling (or may have sold) a Golite Lair 2 with nest for $150 shipped
Shelter: James MacDiarmid is selling a Tarptent Rainbow for $160 shipped
Shelter: Claudia Garren is selling a brand new Tarptent Contrail for $180 shipped
Shelter: Matt Saunders is selling a Big Agnes Seedhouse SL1 for an incredible $130 shipped!
Sleeping Bag: Thomas Conly is selling a Thru-Hiker Quilt for $225 shipped
Sleeping Bag: David Stenberg is selling a Western Mountaineering Megalite for $215 shipped
Sleeping Bag: John Devitt is selling a Golite Adrenaline 40* bag for a super cheap $125 shipped
Slim Pickings on packs on the gear swap now, but keep checking, as they come and go.
Pack: Dayla Austin has an older Dana Designs Racer X for only $50
Pack: ProliteGear.com has the Granite Gear Vapor Trail for $128
For a sleeping pad, get a 12.75oz $25 Thermarest Ridgerest.
Sell the Camelbak Bladder and get a Platypus if you really like the hydration system, or use Gatorade Bottles.
Drop the separate cup.
You don’t need an extra shirt, especially with wool and being out west. If you have to have an extra shirt to sleep in get the lightest weigh synthetic shirt you can find.
Those socks seem really heavy to use with trail runners. Most people use something like the Smartwool Adrenaline socks that are 1.9oz each.
Most people find they don’t need liners with trail runners.
Repackage the Hand Sanatizer in a mini dropper bottle.
I would drop the towel since you already have a bandana
I would drop the Ipod
Do you really need a GPS? You already have a map and compass.
I would go with a lighter knife. Something like a Ultralight Gerber LST or Spyderco Ladybug. They are relatively cheap and only weigh 0.6oz.
I would repackage your sunscreen in a smaller container.