I may have just answered my own question. The starboard is already attached to your transom isn't it?http://classicaquasport.com/smf/Smileys/fantasticsmileys/oops3.gif
The Starboard is kind of soft. My guess is, the screws would eventually wear out the hole. You could always instal threaded inserts like these: https://www.boatoutfitters.com/8-32-press-in-threaded-insert?gclid=EAIaIQobChMI3ubr6e2O2wIV3rjACh2M6QHSEAQYASABEgLM2PD_BwE
You can actually get a good bond useung 5200 with Starboard. Just rough it up. I’ve even used a table saw to kerf the back of Starboard blocks for mounting accessories. It also helps to pass a torch over the surface of the Starboard, not enough to melt or char, just to alter the surface for bonding.
Why not use say 3/16' stainless nyloc nuts & bolts with the bolt countersunk & inverted?
How about a hanger bolt for such an application? Certainly won't spin.
There is also a stud you can get that has wood screws on one side and machine screws on the other side.