
"An indispensable, comprehensive, yet highly practical and easy-to-use tool... it includes vital information on basic and crucial aspects of sophisticated manufacturing processes, along with applicable industry standards"--Back cover.
For machining, I’d start with wood (wood lathe or router, cheaper than a real metal lathe or mill). Very similar concepts as real machining (feeds and speeds, toolpaths, CAM). Up to you if you want to start manual or CNC. The Shapeoko routers are very nice and relatively affordable (in this domain). You can also find used manual machines locally, but it’s hard to know if they’re in good condition if you don’t know anything.
If you want to read, the Machinery’s Handbook, aka the Bible in any shop, is enormous and contains pretty much anything you’d want to know.
Oh, and get a set of Mitutoyo digital calipers. Expensive but the only way to go, in my opinion. Measuring is fundamental to manufacturing.
You can go through a lot of end mills cutting dry. This is less of an issue for hobbyists who aren't turning large volumes of metal into chips and aren't using high-powered milling machines. The main limit on milling speed is getting rid of the heat. If you're willing to run slow, dry cutting works. Or if you only cut materials softer than steel.
At some point, you get Machinery's Handbook.[1] For most of a century, machinists' toolboxes had a built-in space for a copy of that book. Now it's available as an app.
I've got an old copy, but they tend to remain useful for generations, as the basics really don't change very often. When you've got to make a bevel gear, and all you have is involute cutters, they've got the formula and details to get an acceptable one-off.
If you're cutting an ACME thread, they've got it covered, etc.
If you want to see for yourself, you can borrow a copy from the Internet Archive[2]
[1] https://books.industrialpress.com/machinery-handbook/
[2] https://archive.org/search?query=+Machinery%27s+Handbook
'Machinery's Handbook' is my choice for metalworking.
'Drive to Win' and the other Carrol Smith driving books ('Engineering to Win', 'Tuning to Win') are great for people that want to get into high performance driving.
the 'U.S. Army Field Manual 3-05.70' is a fantastic introduction to survival bushcraft.
GNU's 'Introduction to the Command Line' is good for beginning the life-long journey into *nix CLI expert-dom.
For your question about screwdriver fit, unfortunately that ends up being a judgement call. Be forewarned that for 'phillips' there are identical looking JIS screws [0], it takes a bit of experience to identify what driver to use. Some basic guidelines are, to use the biggest driver that will still bottom out at the tip in the screw, and if the product is of Japanese origin to use JIS drivers. It's very hard to measure, but with experience it isn't hard to tell what but a screw uses. Fit a good quality driver into the screw, and visually check if the flutes of the driver engage all the way to the end of the screen's flutes. Note that you need to use a good screwdriver here, I've seen the cheap screwdrivers ground at 15 degrees off of the correct angle.
And if you want all the specs on a particular screw, picking up an older copy of Machinery's Handbook will give you more detail than you were aware existed.
Although from your question, it seems like you are working with poor quality screwdrivers. Cheap screwdrivers make any screw feel like garbage and strip out stuff, it's worth it to invest in good ones. Surprisingly, harbor freight [1] has a set that I own and I would recommend over my Wera drivers, they are not bad at all. If you want to buy once and be done, Snap-On makes by far the best set [2],although keep on mind that $200 price tag will also need to be supplemented with another $50 Phillips #3 driver.
Or, if you don't need to access screws down deep wells of plastic and can use them, the Bosch replacement bits for impact drivers commonly available at hardware stores are fairly decent, although they aren't as good as the Harbor Freight Icon set linked as the cheaper option. This is one thing where quality costs, and you need to determine if you want/need that quality. But if every screw is feeling soft and stripping, it is almost certainly your drivers.
[0] https://www.amazon.com/Hozan-JIS-4-JIS-Screwdriver-3rd/dp/B0... (I don't have experience with this particular set, I have a Vessel set that is OK but not good}
[1] https://www.harborfreight.com/professional-mechanics-screwdr...
[2] https://shop.snapon.com/product/Instinct-Soft-Handle/8-pc-In...