Depends on what the book is offering:
For opening theory : ditch anything too old!
For books on strategy/positional play: Their age would not matter ... the "recommended" ones will always have instructional value for club players.
For Tactical puzzles: Be a little suspect as the older books had no computer analysis to verify the combinations so you will see mistakes in some of the more complicated problems.
For annotated + instructional games: the OLDER the better! You don't want to mess with anything too modern (especially if you're not a strong player already) until you've gone through the classics.
I've read a few of those listed by you and I've never felt any weirdness in going back in time and switching back to the present ... logical thinking/deductive reasoning hasn't changed much through the years :)
Is it better to read the old classic books FIRST, even if they are more "advanced" than more modern books covering the same topic, just to see the generational progression in chess development and to aid in understanding the game and teaching materials of today?
e.g. Reading Tarrasch's Game of Chess, Capablanca's Chess Fundamentals, and Nimzowitsch's My System and Chess Praxis first (1910's and '20's), then tackling Pawn Power by Kmoch, Modern Chess Strategy by Pachman, Art of Attack by Vukovic, and Chernev's collections second (1950's and 60's), and then hitting more modern books like those by McDonald, Silman, Heisman, and Seirawan (1990's and 2000's) and various software programs) even though it would be argued that the more modern books are easier and more accessible to weaker players and should be read BEFORE the more ancient yet more difficult (and somewhat outdated) books.
It just seems weird that one would read a modern chess book trying to learn something, then go back to a more advanced yet more dated book on the same subject in order to "improve" playing strength.