I've damaged some cabinets too CEFreeman and these seem to be glued really well in addition to the screws. And since it's hardwood to plywood, I'm afraid it would be the plywood that would give. No, there won't be a toe kick space under the oven. That cabinet used to be full height and we cut it down. To get the stove opening at the right place, the drawer at the bottom was cut off, and that's the gap you see at the bottom. I was going to put baseboard-furniture look around the cabinets anyway, so didn't worry about that gap. Thank you mulemom. I had thought of something along that line, but I'd probably have to make it since there isn't much wood taken off the corner. I also thought of routering the other end of the counter so they are both rounded, but then I have to do something to BOTH ends. They might even make bullnosed baseboard.

I understand the purpose of molding along the baseboards. I have shoe and like it. But if you are inexperienced and see lots of pictures of plain baseboards, arrange to have them installed and the installer does not mention quarter round or shoe, you're going to be disappointed. Some people go to the expense of having the base scribed to the floor. Options - or what will be done - should be discussed and in writing up front. No surprises! What I was calling unprofessional was the notion of a 'huge caulk joint'. That is not a professional option. Baseboard gaps are covered with molding not filled with caulk. I would much rather come home to molding than caulk!

An alternative idea: This probably won't work if the wainscot if a thin luan-type of sheet good. If it is real wood, it may work if the bow has some movement to it. Drive an oversized hole in the baseboard. Large enough where the diameter of the hole does not catch the threads of the screw, but small enough where the countersink of the hole still catches the screw's head. Run a deck (NOT a drywall screw) screw through the hole and if the wainscot is of sufficient thickness, the threads will grab the wainscot and pull it towards the baseboard. The patch and paint the screw holes in the baseboard.

Premixed spackle, paintable caulk, M&H ready patch, all would work fine.