I carried out the re-installation of the baseboards by using the WireTracks recommended adhesive and gluing the mitered baseboards to each piece of WireTracks channel cover. I used rocks from the garden to "clamp" the baseboards into position against the channel while the glue dried.
Stone-age solution to holding baseboards in place while the glue dries.
When I first started this task, I was using my cheesy little yellow plastic Stanley miter box and saw. It took me about half an hour to get the first miter cut meeting properly, since the miter box would flex while I sawed, preventing a straight cut, and necessitating a lot of utility knife whittling by yours truly. Luckily, however, my brother-in-law had just bought a nice "chop saw", and was very willing to lend it to me to make my cuts. What a difference in precision and productivity!
Unfortunately, as I feared, it was pretty challenging to get the baseboards reattached with minimal gapping at the top of the baseboard. The problem is especially bad with the outside walls, which didn't have great studs to reinforce the top portion of the channel-back. This allows the channel-back to flex backwards when you press the baseboard back into place, making it very difficult to get it "snapped in" properly. I finally ended up sitting on the floor and kicking with my feet to slam some of the more problematic baseboards back into place (made me glad I didn't paint the baseboards before reattaching them!). (NB: this kicking at the baseboards with my heels gave me a nasty case of plantar fasciitis, so keep that in mind if you're susceptible to it at all).
There's not much to say about the painting - it followed the caulking. Rather than caulk everything first, then paint, I painted each caulked section as it dried.
I have to say, that even with the struggles I went through in getting the baseboard into place, once caulked and painted it looked great. The contrasting wall and trim paint looks snappy and my caulking was good enough (surprisingly) to hide the gaps at the baseboards. A friend came over and commented that it looked professional, which was good enough for me :-).