Been years since I played this game, but back then it was sometimes difficult to keep it rolling perpetually. For example, around back to school time they used to (maybe they still do) offer backpacks that were FARewards, which included some of their more high-end models ($150+). If you took advantage of that you then had to find a similar value in FARewards items to spend that on before it expired, which wasn’t always possible so if your goal was continuous rolling you had to pay some consideration to what their future offers were likely to be and that wasn’t trivial since weekly ads and pure speculation were really the only source of this information.
OM never allowed you to buy OM gift cards (although IIRC they once cancelled an online order I placed and in refunding my purchase I believe the rewards portion was ultimately refunded to me in OM gift cards, which had the benefit of not expiring – not sure if that’s still the case). Also, back then you could use the rewards to purchase 3rd party gift cards in-store if the clerk didn’t stop you (I suspect that loophole has been closed by now, but perhaps not). One downside this was that it did effectively lock in a sales tax loss for you. What I mean by that is you paid sales tax on the original purchase and when purchasing a gift card you’re not going to negate any sales tax on that purchase the way you would if buying physical merchandise.
Assuming 3rd party gift cards have been disallowed you’d then be stuck trying to find some item you could resell at either a profit or a minimal loss or some item OM sold for a reasonable price that you actually wanted to buy (a surprisingly challenging task). Back then they sold the Ooma and it was reasonably priced and sometimes they’d have decent deals on printers, but finding such items were far from trivial.
As to case paper, I can’t say the time involved would be justified, but it wasn’t hard to resell a case for ~$20 on Craigslist.