I think its a great idea tbh. Once the groundwork has been done it'll be a lot easier to simply tweak everyone's stats and update information, such as title histories, as databases are released.
For example, a January 2002 update would still have Brock Lesnar in OVW with fairly low popularity but a strong look (not entirely sure what the terminology is in TEW20). By the July 2002 database, however, he will have debuted on the roster, won the 2002 King of the Ring, and need to be in a position where his WWE title match against The Rock at Summerslam looks feasible. His popularity will therefore be much higher, though his stats might not need to change as much. Then compare that to a 2019 Brock Lesnar, who would presumably have better psychology stats and the like, which would have gradually been increased over time.