All Calls Randomly Drop about once an hour - Everything works as it should otherwise

You’re using the term ‘roll back’ incorrectly here, I think. There is no ability to ‘roll back’ because nothing is touched on the original machine. This means there is nothing to ‘roll back’ to.

However, yes, CDR records are not moved across, because they’re super trivial to do yourself and it does not need to be automated.

(It’s ‘mysqldump asteriskcdrdb > file’ and then ‘mysql asteriskcdrdb < file’ on the new machine)

Is this your only issue?

Edit: If you want me to add cdrs to the conversion, I’m not TOTALLY opposed to it, but doing that that will SIGNIFICANTLY increase the length of time it takes. CDRs can be copied at your leisure, without any issues at all.