At the end of August, there won't be any bugs. The nights will also be cold - like lower 20's. Yes, there is a LOT of wind. Fortunately, the monsoon season will be winding down, but it will rain so dedicated rain gear - top and bottom - is a wise investment. Up high, that can be a very cold rain.
I would suggest you:
1- add a pair of dedicated merino wool sleeping socks. Your feet will love the clean dry covering and your sleeping bag will smell nicer too.
2- add a pair of merino wool or synthetic glove liners. Your fingers will love you. A pair of WP overmitts will be a welcome addition for rain and wind.
3- add a wide brimmed hat. The sun is quite intense above treeline and sunglasses alone won't cut it.
4- you only have two platypus bladders of unknown size. You'll need more capacity than that on some sections south of Salida. I carried 3 one liter bladders (one on my Hoser system and two spares) and one wide-mouth one liter juice bottle (for water being treated). Platy bladders are very hard to fill from a stream. The empty one liter bladders cans stay rolled up in your pack until needed.
5- your REI trekking poles are 19 ounces. If you can afford it, consider the Gossamer Gear LT4 carbon fiber poles - 8 ounces the pair. I've used them on the PCT and CT for years.
6- I'd replace the mini-groundhog stakes with the full size versions, at least for the front and rear guylines. It's very windy above treeline and your tarp will need all the anchor it can get. Tent or tarp is purely a personal choice, but if you tarp, make it large enough to give you and your gear good coverage from the adternoon rain storms; they can be intense.
You're starting from Breckenridge to save time, so you'll ultimately have to return to finish the first 6 segments anyway. That said, consider one of the two following scenarios: If you're interested in the map and logistical details, PM me with your email address and I'll forward it to you.
1) Start from Copper Mountain Resort in segment 8 instead. The trail runs right behind the Burning Stone Plaza at the resort.
2) start from Breck (Gold Hill TH) as planned, but slack-pack segment 7 and that God-awful hill between Breck and Copper Mtn. Take the free bus from the Passage Point stop at Copper Mtn back to Breck to retrieve your gear, stay at the hostel overnight, return to CM the next day and hike on.