As it's a migration there will almost guaranteed be issues or things you didn't expect.
The best approach is to first make a backup of your site. Next clone your site and upgrade the clone. This will give you an idea of what to expect. If you've any 3rd party extensions integration with CB or any system plugins for CB installed be sure to disable them (e.g. Kunena integration plugin, K2 profile integration, CBSubs system plugin, admin nav module, etc..) to avoid API load order bugs.
You may also want to watch the below video.
Additional CB 2.x videos can be found below.
www.youtube.com/playlist?list=PLp0puRITgC7PuyzPsMUECDI46VE7IFSAX
Be sure to become familiar with CB 2.x and its changes on your clone before deciding to upgrade your live as it'll better prepare you for any unexpected behavior.