I have a pool with repressed clay brick pavers around it. I need to drill holes to insert loop lock pool cover anchors.

the anchors take a 3/4" hole, and have a 1/4" tall shoulder at the to which increases the diameter to 27/32".

Will a carbide tipped masronry bit be sufficient for this application? Do you recommend pilot holes? Should I start the 27/32" (or 7/8") hole first, then continus with the 3/4" hole?

Will the hammer function brake this type of brick?
Thanks for your help.
Dennis