So I realized that no dolly will work as good as transom wheels. My concern is when I drill holes for the wheels what sealant do I need to put in the holes and how long does it take to dry? I do not have a driveway
You could paint with epoxy or enamel paint hole interior. Once dried, apply silicone to bolt's threads and slide in transom, adjust tight, when done apply silicone at both bolt sides to avoid water intrussion that will end rotting transom down. Let cure at least for 24 to 48 hours.