Wow, thanks for the detailed reply on the books. So after my previous post I ordered the Lipton book last night and just got it today (Amazon is awesome, been making me poor since 1999 lol). I haven't started reading it yet but I it seems like just what I was after.I would pass on the bedside reader for now. People charge a lot for it because it is out of print and fairly popular, but it is not exactly information-dense. I found the three volumes to be enjoyable to read, and might do some of the projects, but a lot of the information was either obsolete (e.g. where to buy a specific lubricant or emery cloth) or has become common knowledge.
Machine Shop Practice is worth the price (which, as pointed out, is low) and thorough, but it is a bit dated. The book I wish I had started with is Technology of Machine Tools (the earlier the edition, the cheaper it is), which is basically a textbook for shop class.
Lipton's book is excellent. Of the "tricks of the trade" books, I would probably order them (best to worst): Bulgin, Lipton, Harvey, Marlow. The Marlow ones are neat to have in the shop because of their format, which is Q&A, but the information in them is basically right out of machinery's handbook. The downside of Bulgin's books is they are pricey, and the information is dispersed over something like five books (the "building shop" series and the lathe and mill books).
Recently enjoyed Spitler's Fundamentals of Tool Design. Currently waiting for Bradley's Shaping Machine and Lathe Tools to arrive from overseas. In case you couldn't tell, I'm a bit of a reader
After reading your suggestion previously and @Bill_729 's validation as well I'll add the Moltrech books on my wish list and then possibly the machine shop practice (the second edition since it has a section on CNC). Bulgin's has a set of 3 books it seems and they look interesting too. I wish I didn't invest in some of the books I posted above as they weren't for me.
As for the book smart part, yes I agree 100% but since I don't have any formal training nor a ton of practice time (machining is just one of several hobbies) I do like to read tips&tricks types of books on the days when I'm traveling/relaxing etc so I can pick up useful info from folks who do this for a living.