I do the work on my motors in the water but then my nacelles pivot. I don't think you will get the motors vertical if you pivot into the dinghy but you don;t really need to for draining. You may for filling though.
Beaching is a really important facet of owning a cat. Choose a nice flattish beach out of the wind and waves preferably. A nice big flat oil tray underneath and plenty of rags and a plastic bag should be good for cleanup.
I like my Yammie 9.9, it is a good bit of kit. I would also consider buying an oil changer from Bunnings. It does well with a smaller tube taped on for the 9.9 motor sump oil. Much better than draining from the plug. Do this often and your motor will be nice after a decade - mine still is purring along.
www.bunnings.com.au/briggs-stratton-oil-removal-kit_p3370025cheers
Phil