Looks pretty good.
D1 and D2 are backwards, and I'm not sure if the reset pin can be floating.
Push some traces so they don't come off the pads in an angle.
No you don't need the USB to be length matched in this case.
The reason you can't get it to work is either that it's too short and constricted, or it's not properly set up. Length matching in Altium is black magic. It only seems to work when I don't know why.
You could however make those tracks 10mil too. Wider then the pads looks kinda off.