1- After Sawmill, probably something like a couple of months later. All the videos are made and released in chronological order (barring the occasional flashback, which episode 5 will have a couple of, set before the rest of the series).

2- Oh, I never really thought about Watchtower and Sawmill, um... I'm far from an expert in US geography, but I would imagine they're meant to be in the northern foresty parts of the state, maybe close to or even past the Colorado border?
I haven't settled on a clear location for Like White on Spy, but one of the inspirations for its desert road setting was Fallout New Vegas' Mojave desert. I believe western NM is similarly flat and desertish though, so it could be set closer to the rest of TF2's setting than way over in California / Nevada.

3- Ehm, I suppose it's a combination of him being a gentleman, her being his type, aaaaaand maybe something else I can't really mention just yet ;)

4/5- You'll have to wait and see ;P

And yeah, I do still plan on posting stuff to the announcements section, I've just been pretty focused on working on the fifth episode proper lately.

Oh, I forgot about one question:

While Team Fortress 2 is set in 1968, is it the same case in your videos?

Yep, they're set during the Gravel War.

E