Huan,
since you wrote "drop some cash to upgrade and/or purchase". I will make a couple of suggestions that will require some cash.
First the "cheap" suggestions for things you might want to leave at home:
1) Survival bracelet – 0.8oz
2) Midlayer Jacket – 10.8 oz (use a down jacket)
3) Short – 4 oz (you have convertible pants)
4) Extra hiking shirt – 4 oz (wash your other one along the trail on a sunny day)
5) Sleeping socks – 2.2 oz (use your extra pair of hiking socks)
6) Nalgene – 4 oz (bring a 20 oz Gatorade-like bottle instead)
7) Compass – 1.15 oz (in my opinion not needed on the JMT)
8) GPS – 7.35 oz (in my opinion not needed on the JMT – I carry one nevertheless to record my track and analyze it later)
9) wallet – 4 oz (just carry some cash and 1 credit card in a ziplock)
10) 1st Aid – I won't argue with a nurse, but I think you can get it down to 4 oz
That saves you already 42.3 oz. Not too bad – over 2.5 lbs gone.
Now some upgrades
1) Trekking Poles: Gossamer Gear LT 3 – 5.6 oz (saves 15.4 oz)
2) Rain Jacket: DryDucks – 5.5 oz (saves 5.3 oz)
3) Shelter: SMD Cuben Haven (10 oz) + GG Polycryo groundsheet (1.6 oz) or ZPacks Duoplex (19.3 oz) if you prefer protection from bugs – (saves 24.4 oz)
4) Backpack: ZPacks Arc Blast – 16.5 oz (saves 40.5 oz)
Now you saved another 85.6 oz – over 5 lbs. Your total savings is now 128 oz or 8 lbs.
Some of those 8 lbs will now be spent on some purchases
1) Bear canister – Bearikade Scout – 28 oz (with resupplies in TM, and RM this should be fine) Ideally you would get an Expedition and share the 37 oz canister. The same is true for the two person tent above.
2) Down Jacket – Today is a great time to buy the Golite Bitteroot as it is only today on sale – 13 oz
3) Down quilt – Take 20F as you are going in June (normaly I take a 30 F) – Zpacks (16.7 oz) or EE Enigma (16.5 oz)
4) Sleeping Pad – NeoAir XLite – 12 oz (take the full length)
Now you added 69.5 oz back. That leaves you still with a saving of over 3.5 lbs.
Other things I would personally add. Bring a Tenkara Pole – for 2 oz + 1 oz in accessories you add a lot of fun to your trip. A buff and/or a merino balaclava and/or a down hat (like black rock hadron) to cover your head while sleeping or while sitting in camp. Personally I prefer the SteriPen Freedom over Aquamira drops. It weighs only 2.6 oz and saves me from carrying a lot of extra water that is treated. All I need is my 16 or 20 oz bottle and I can drink right away. The battery lasted me 7 days on the JMT. If you bring a USB charge cable you should be able to charge at RM while resupplying there.
Going with 5 friends sounds like a cool trip. That in itself gives you a great opportunity to save some more weight by sharing tent, bear canister, cooking gear, etc.
Have fun out there!
Manfred