I don't find the list of manual to-dos too daunting. An Oracle upgrade is way more intricate :) Can you detail the steps you had to take for the packages? - We should address every single issue.
What about templates? The templating system behaviour has changed and I haven't yet seen any mention of noquote woes.
Well, it is not daunting, but the system you get needs a lot of baby-sitting if you wish... For one, I cannot seem to be able to upgrade sub-site easily -- will most likely have to try and replicate a setup from another 5 instance.
Also, this is a very small instance -- only a few applications are used and there are only a few users. Not sure what would be the impact if one were to move openacs.org...