I also use a Kobo with Calibre-web and it syncs fine. It’s been about a year so I can’t remember specifics. I remember modifying settings in my Kobo to point to my Calibre-web URL and in Calibre-web settings allow Kobo sync and then make a Kobo shelf. All the books in Kobo shelf are what it syncs too
I have a sawstop PCS also, and I still can’t man handle a full sheet of 3/4 on it. I find my track saw is better at handling sheet goods. Do you have an outfeed table or something else to help?