Which one do you like better and why? Considering upgrading our 4.4.3 to 5 something…
I think it depends on what you need. If the 5.x series has new features or bug fixes you want then it makes sense to move to it. If you’re just happily filling in and resolving tickets under 4.4.x there’s not that much difference in 5.x to be honest.
Why stick with an old major version? The update to version 5 work just fine for us.
About the only reason I see to stick with 4.4.x is that not all plugins are ready for 5.0 yet.
Most are okay, have been absorbed into core, or have a 5.0 branch.