I have a couple friends who have them and they are big fans. One of the guys even bought a kit to adapt a pedal-powered bike into an e-bike with pedal assist. Those things can haul! Perfect for the short trips you mentioned.
Just know that the transom has to be REALLY bad to show flex when putting weight on the outdrive. My transom was substantially rotted and showed no flex at all.
I agree with @alldodge . I don't know that a dentist pick would get through the fiberglass layer. It also wouldn't show if the wood fibers were light colorred and dry vs. wet and dark, like the drill test would.
My boat had water intrusion from swim ladder bolts that were below the waterline but were not properly sealed. Four holes - maybe 5/16" each. The entire starboard side of my transom was rotted and water migrated to the deck thru the wood fibers and rotted much of the deck on the starboard side...
Lots of good answers. I would add that it's a good idea to get things apart before you start ordering supplies. It's often cheaper to order in bulk and you need to know exactly what you'll be replacing. And don't skimp on the personal protective equipment (PPE); fiberglass and resin in your...
We beach quite often and I put on one that a bit longer than recommended, so I'd agree with @Scott Danforth in post #4.
The keelguard does a great job of protecting against sand scuffs. Even better, we hit a rock ledge at our lake in Ontario (water was unusually low last year) at slow speed...