Yes, the superblocks will have higher difficulty and the record holder would have the highest, however if more than one of them share the same top difficulty you'll have to decide by comparing the value of the hash of the block's header (in the bit order that is used to generate the base prime), or just compare the base prime for those.
Hi gatra, do we have to roll the timestamp as frequently as before with the new super block stratergy?
Yes: maybe less frequently because larger numbers mean that looking at all the nonce space may take a little longer, but most likely the difference will be too small to be noticed.