Louie....With the Contour2 remote, there is a button A that is the TV online HELP...do a page up/dwn to view various features. Not sure what the Contour1 remote has. Make a list of "must have" features, then check the forum searches; post forum questions or even go/send email to the COX website and query.
Unfortunately there is no exact method for evaluation. The cost of the update should not be large, except if you have tons of stored shows. Do some homework and make sure you feel good about any update. Of course, there could be other reasons why the update experience could make you unhappy because some hidden feature no longer exists.