While it may be a petty complaint, having been in the real Anchorage many times I can't help but wonder if the good folks at Bethesda ever spent more than 5 seconds researching a map.

It appears to be set in the mountains to the East of Anchorage and then in the Rabbit Creek/ O'Malley Road area. While the flat-land portions are possible, there is no way these mountains could be the same ones that are there.

I understand that a lot can change in 55 years (and that the Fallout 3's alternate reality timeline diverged from our own some time prior to the present). I also realize that it is supposed to be a simulation and the General himself was dissatisfied with the simulation's accuracy. But really.

Well, Gen. Chase was not only dissatisfied with the simulation, he was also mentally unstable. There is a research terminal in the Outcast Outpost that says Gen. Chase frequently changed tactical data, environment layout, and he was overly dramatic and theatrical with the story. So in the end, I wouldn't blame Bethesda because they probably intended it that way.

Yeah General Chase was....different. In his later years he went bonkers and began glorifying his actions in the Anchorage Reclamation and as Liongrowlboy stated, the virtual reality reclamation simulation was completely out of touch with reality and is stated to be as such in game ( I wouldn't be surprised if ol' Constantine just "made up" those cliffs to make the actions of Montgomery and whoever seem more heroic). I suppose you could make the arguement that Bethesda "didn't do their homework" or "didn't give a crap" but the argument also could be made that "in-game" the simulation is stated to be inaccurate (veritbirds appearing when they weren't even in prototype stage by then is one good example of what he changed).

I think that Bethesda wanted to do two things, 1. create an inventive life story for Chase, and 2. Just make the simulation more fun and dramatic to play through, in game reality, the actual Reclamation of Anchorage probably wasn't nearly as fun, fast, or easy

Getting into bed with Straun(figuratively speaking, of course) is another example of his mental instability.

Also, who's to say the geography of the entire world isn't different than ours? It is an alternate Earth after all.

Yes, I also think that's part of it too.