Hi Brad,
I was in the Winds ~ Aug. 22-28 or 29 (don’t remember exactly which day we hiked out).
Road: We drove in to Green River Lakes and out Big Sandy. No issues. Roads were fine, not overly potholed, a bit washboardy (is that a word?) on parts coming out of Big Sandy, but not bad (we were in a Dodge Caravan, I believe).
Creek crossings: Nothing bad. The CDT likes to go right through creeks, so we had to ford a couple of them, but nothing that got up to our knees (a bit above mid-calf on one).
Bugs: Not bad at all. We had a few in a couple of places, but most of our hiking seemed bug-free.
Snowfield: Sorry I can’t be of much help here. We went over Knapsack Col, which had a bit of snow, more on the Titcomb Basin side than the Peak Lake side (we had a short but fun little glissade session coming down the Titcomb Basin side). Later in the trip we camped a few miles from Shadow Lake on what turned out to be our last night there. We were planning on going over Texas and Jackass passes, but sleet/hail/rain/snow started falling on us around 3 am and didn’t stop. I got a weather report on my inReach in the morning, and it called for the possibility of heavy snow with a winter weather advisory – something we weren’t really outfitted for – so we decided to walk in to Big Sandy instead. We had sleet, then rain, falling on us for a good bit of the walk in.
Hope that helps some. Below are a couple of pics of Knapsack Col, from both sides, to give you an idea of what snow was like at that time (our third day of the week-long trip, it had rained pretty hard the night before, so there was a bit of new snow up there, but this was well before the end-of-trip winter weather advisory).
Looking up at the Col.

Looking back from partway up the Col.

Coming down the other side.

Another view of coming down.
