I didn't know there was an Odoo community I should've been subbed to!
Do you have a lot of customizations? If not, I've heard OpenUpgrade can usually handle things fine.
As soon as you have customizations, things get dicey. Odoo loves changing things around, sometimes for seemingly no reason. Of course this is also a good moment to evaluate the necessity of any customizations - maybe you don't need to port them all over?
Also this goes without saying, but don't run OpenUpgrade straight on prod. Create a database copy to test on. Always have backups.