Slow progress, but progress....
Got the holes drilled into the door for the new rubber boot and speaker wire. Going to pick up some touch up paint tomorrow to paint the bare metal to protect it against the elements a little. Drilling was not as simple as hoped, but not crazy. Had to remove the door card, then pop the molex plug out from inside the door to make sure that none of the factory wiring was going to be impacted by the drill. Once that was done, the metal is 2 layers, which made drilling not quite as straight forward, but not terrible either. Getting the doors off and back on was actually incredibly simple.
Here's a better shot of the grommet on the kick panel side of things:
And here is why I was not going to even attempt to drill the molex, no way was I going to be able to get 3 sets of speaker wire through there.
So, next is going to be running some wire towards the trunk. I can't deaden the doors just yet, there is a recall on Volvo door latches, which the repair involves them stripping the inner door entirely to get to the latch. If I put deadening over there, then they will have to rip it all off. I am slightly reluctant to even put the speakers in to be honest, but apparently Volvo will not even have parts until April.