Tommy just had one of those earlier this week, with the 1/4 round on top of the carpet. A former carriage house behind an old Victorian home which was converted into a duplex. When measuring, I questioned whether the 1/4 round was on top, but felt how far out the tackless came and decided it was not so. Apparently it was super wide strip, because my decision was wrong.
Tia
Ha ha, yea it can get ya. Last one I had like that was thirty years ago at least. I hope they've all been taken care of by now.
The carpet was a wormy looking fiber, low pile, kind of a precursor to the frieze. Plus reeeealy old dirty hair pad.