I'm going to answer my own question.
Yes you can drill out the plug, and its pretty easy. Just use a 1ΒΌ" hole saw with a long shaft. There's an initial lip to get through with the hole saw, then with a little slow and steady effort, the "pinched plug" can be drilled out. On the right side, with the plug removed, you can see all the way to the cat. The only problem I had was fishing out the plug once it was drilled. But with a long magnet and some long reach needle nose pliers, I got them both out. Sounds pretty good now too. Here's a pic after...
I took a completely different approach... having also performed this on my '08 DWG.
After taking off the extension tip on the tail pipe, I used my dremel to cut and then grind smooth the two spot welds holding in the baffle assembly. Once this is done, you can (with minimal effort) remove the entire baffle... just remember you'll need to pull out the glass as unlike the DWG, the screen that separates it from contact with the baffle is not welded to the outer portion of the tailpipe and if you fire it up... you'll have to collect all off of the glass that's blown across the driveway. Don't ask me how I know this

Once done pulling the baffles and glass, just put the tips back on and you're done. I've had many compliments on the sound quality, and am often asked what kind of pipes are they and where did I get them... after explaining the process, they understand why I've chosen not to pay upwards of $500+ for a non baffled slip-on system that does pretty much the same thing. Still, you need to 'flash the ECM, or get it tuned to offset the leaner conditions that come with opening the flow. My gas mileage did not suffer, in fact it went up a few mpg... being lean or too lean in Alaska's weather conditions do not appear to be hurting (running hot) the engine, but why take the chance.
And, no... they are not as loud as some well put together 'premium' packages out there, but it definitely sounds like a Harley, and can double as a horn in traffic with a simple twist of the throttle.
