also,could dreamselves not go through the process of entering the medium?

Technically it’s not about the version of the Player, rather than the Location that’s transported to the Medium. Jane, Dirk and Roxy were all Dreamselves when they went into SBURB, and they all went in through Jake’s Land- But they still had their own houses go into SBURB through Robot Shenanigans, so it’s not like the problem you’re posing at all.