Just in case you haven't heard enough of my thoughts ... lol
Have you considered removing the existing dogs and drilling/reaming a new hole for a tight press fit of hardened pins?
IW
I have been following this thread since it's inception, just to see what you eventually decided to do. This^ post is the best Idea have seen so far, all you would need is a 10mm drill and a way to jig up your gears at that 2 degree angle. Then just drop some 10mm hardened steel pins in and lock them in with flat spotting or possibly a set screw... I'm taking machining classes at my local tech school, so I'm not an expert like a few people in this thread, but it made sense to me.
The first thing to deal with if something along this route is to be followed is that the gears should really be annealed. Even if these are made from a lower carbon steel and just case hardened, that's still maybe .060 of hardened material you'd need to get through. They could be 4140 or such that could be hardened through. Drilling hardened materials (like HRC 55 or so and below) is possible with carbide drills (expensive) but as has been stated in this post already, carbide demands certain conditions and one of those is even cutting pressure which you really can't achieve using a manual quill. This doesn't have as much to do with the rigidity of the machine as it has to do with the rigidity of the arm. It's not really possible to maintain a constant feed by hand, you might get off to a good start, but if you hiccup along the way, often you're toast.
Seems like if you were going to go the route of drilling and pressing new pins in, you'd be doing that to avoid having to setup funky angles and the difficulties of indicating your position at that angle. If you're flat and you've got that nice round dog sticking up, you can sweep it with an indicator and center on it really easily. Once you're at an angle you're dealing with an oval so sweeping becomes taking an average. There's ways around this of course, tooling balls or a jig with a location method included, but the more complicated you make things, the longer it takes and the more chance you have to introduce error.
Then even if you drill out and press in pins that you had an angle turned on by somebody, then you've still got to setup and machine the mating surfaces on the matching gear. After that you'll need to re-harden and temper the gears.
Some good reading on backyard metallurgy (post number 7)
http://www.practicalmachinist.com/vb/fabrication-cnc-laser-waterjet-plasma-welding-fab/surface-hardening-oxyacetelyne-132029/