Sometimes the bolts sticking through the panel beneath the fender get bent downward or have been re-installed improperly by a previous owner, creating a small enough gap to make getting the welting to fit tightly challenging. One car I restored years ago had 1/4" bolts that some "restorer" had pressed into service, which really made installing the rear fenders and welting a nightmare. 'Kind of indicative of how the rest of the car was put together. You could use a rat tail file and extend the fender holes along their bottom edges enough to raise the fender sufficiently. This shouldn't be necessary to do, but after 90 years on the road and passing through the hands of many past owners, nothing will fit the way it did at the factory.
Marshall