So I deliberated for a while and even considered putting some sort of reinforcement "rib" in there to spread the sides out. That seemed like way too much effort, and I hadn't heard about other builders doing that. So what I ended up doing was taking the fiberglass piece into my kitchen.
I set up an ice-cold water bath in a pot...cold water with a buttload of ice cubes. I then ran the fiberglass piece under scalding hot water for a few seconds, spread the piece open by hand, stretching it a bit, and held that stretched position as I dunked it into the ice bath and let it cool. I did this a couple of times, one time using wooden blocks to spread the sides, until the piece showed a visible and measurable widening.
When I finally drilled the tip to the rudder, it wasn't perfect, but it snugged up enough so that as I clecoed each hole it got snugger and snugger. It worked out fine. Here's a shot of the fairing after being drilled and clecoed into place.

Then it was through the motions of dismantling, deburring, dimpling, countersinking the fiberglass (with my now-designated fiberglass specific bits), and putting it back on with clecos. A couple dozen blind rivets, and this sucker was done. Looks good...ready for filler.

I'm dreading the lower rudder fairing. That's going to need some major trimming and I can already smell the iterations. I might move on to the elevators and horizontal tab for now. Better yet, I'll leave it for the future. Hell, this filler needs 70-77 degrees Fahrenheit for ideal curing setup, and it's about 60-65 degrees here this time of year. Plus we're moving, so I think fate is telling me to wait just a bit.