Originally Posted by
Jim from Boston
My beater bike has a rear rack, and I had a Jandd trunk bag for years, but now I have an Ortlieb roller pannier bag, and I think it meets almost all your requirements, including in contrast to the trunk bag described above, it may well fit a Macbook, and is easy to close. All the other good features apply, but no rear light attachment, though a brightly reflective triangle is on both ends.
It served me well, with enough room to carry all the extra stuff during Boston’s historic brutal winter.
+ 1 on Jandd (and ortlieb) gear but most of it is outside the op's price range. The Jandd duffel rack pack works very well and holds a large volume of stuff but it's not waterproof:
Duffel Rack Pack
Jandd stuff is very solidly made and the company does an A1 job of standing behind its products.