I think they have some incredibly low pricing for what most small companies need. I also think they've done a very good job of carving out pieces that more sophisticated setups need into the enterprise tier, which does constitute a big jump.
One that bit me was https://developers.cloudflare.com/cloudflare-for-platforms/c... - we found an alternative solution that didn't require upgrading to their enterprise plan (yet), but it was a pretty compelling reason to upgrade and if I was doing it again I'd probably choose upgrading over implementing our solution. On balance I'm not sure we actually saved money in the end, considering opportunity cost
One that bit me was https://developers.cloudflare.com/cloudflare-for-platforms/c... - we found an alternative solution that didn't require upgrading to their enterprise plan (yet), but it was a pretty compelling reason to upgrade and if I was doing it again I'd probably choose upgrading over implementing our solution. On balance I'm not sure we actually saved money in the end, considering opportunity cost