First, I don't know that it's possible to buy new Rebels anywhere. And that's a damn shame...
But if somehow you can:
Yes, the side pocket can fit a hoodie...and a hat. You won't fit much else on that side, but yes. I live in the Northeast, and this is my year-round bag
I generally carry 16-17 across the main compartment, plus 5 in the vertical shelf pockets (total 21-22). I could slip a few more distance discs in if I had to, but I think 26-27 is the practical total without also using a side pocket.
I can't speak to customer service, as I've never needed it. I understand your concern. After a full year of use for me, the bag is fine.
Regardless of what bag you're looking for, I have one suggestion about a feature to look for, and that's a sturdy, dedicated handle. It's honestly the "most used" feature on a backpack, and I think it gets overlooked. My previous bag was a Fossa Skinny, and as much as I liked the bag, the "handle" was just a sewn gripping area where the tops of the straps met up. I never really liked it, but didn't realize how inadequate it was until I got the Rebel. So: look for dedicated handle/strap that seems sturdy enough made to pull on a couple of thousand times.
Good luck!