That Stuff Goes in There?!

So this is my <20 lbs of stuff that has to go in that Osprey Stratos 36 pack. Will it fit? The extra pair of shoes (HOKA Speedgoat boots, and necessary) will hang off the back in a rain bag. Yep, it's forecasted to rain the first couple of days we're on the trail.

I have been through narrowing this stuff down 5 or 6 times. I'm sure after carrying all of this for a few days, I'll be giving stuff away!