Check the webcam at Tripcheck.com for the Santiam pass. It shows quite a bit of snow. The good news it is melting off at that altitude, 4817', and should improve all week. Ted was xcountry skiing at Ray Benson snow park last Sunday and had 18-24" of snow.
When I rode 99 about a month and a half ago, it was a mess. I haven't heard about anything changing up there.
The forecast was for mid-60's up at Bachelor today and still warm for part of tomorrow. I would be super stoked if enough melted to get one last flagline run in... see Nat, I do have a little optimism in me :-)
So far as I know all 120 miles of Metolius-Windigo were clear of blowdown as of late summer.
As of the BBFT Flagline was rideable, but marginal. As of last Sunday the snow level was around 5200 feet and Phils' behind the helipad was largely on snow. With this week's warm weather (Bachelor's web cam shows bare spots on north aspect at 6300 feet) I'd suspect the North Fork-Flagline loop to be doable next weekend if you're willing to put up with getting majorly muddy and quite possibly a few miles of hike a bike in the trees on Metolius-Windigo and Flagline. The trails are soft and getting cut up around 5000 feet so I'd bet on a pair of hiking boots and gaiters instead of bike shoes if you want to go up around 7000.
Yeah, that's something of an approximate definition of clear. But every section I've been on this year has been clear to the extent normal for a bike trail, and that even includes a little bit of hiking on the wilderness stretch around Cultus that's closed to bikes. I got to see some FS trail data which said more or less the same thing, but I haven't personally been on all of Met-Win. So there could be unmaintained sections I don't know about.