I will try & address a few of your questions. As to bobbins for the #8 machines "Most" of them use a bobbin that is 1 inch 25.4mm) in diameter & a [plain case which has no tension built into it. The lower thread tension is applied externally of the bobbin case. Late #8 machines use a bobbin which measures 22 mm (.866") in diameter & the case has a built-in tension spring. This same bobbin & case was carried over to the early #9 machines, but very shortly a locating finger was added to the case.
I did a write-up on the bobbins & cases for the files section, it is found on page 2, also on page 5 of the photo section are pictures of all the various bobbins & cases used on the W&W family machines, & also includes the Singer built 9W machines.
As to the carved attachment boxes, I have never seen these with attachments for other than the #9 or D-9 machines. The shanks for the #8, #9 & D-9 attachments are all the same "Except"; The #8 simply has a hole through the shank for the clamp screw, so the screw has to be removed to change feet. The #9 & D-9 feet are both slotted so the screw only has to be loosened & the attachment slid out the side. However, the slot is on opposite sides for the D-9 from the #9. Any of the feet "can" by a bit of manipulation be used on any of these model machines. The #8 was intended for use primarily with the glass feet so was not necessary to remove the foot itself in changing. While an insert foot was made for the #9 it also introduced more dedicated feet which did require changing, so made the detach & attach quicker & easier by the slotted shank.
The #9 machines used the hinged bobbin holder with a removable case, W&W called the holder the bobbin Drop. The D-9 came along in 1895 & used a built-in bobbin case with a latch finger. The case was not removed in changing bobbins. The Singer 9W retained the case of the D-9.?
On the #8 with external tension, it is "Absolutely" Essential that the bobbin is placed so the thread comes off the bobbin from the bottom toward you & thus up in front. If you put it in the other way the thread will miss the tension & you will simply get big Rat's Nests below the cloth.
If I can help you with any other questions do feel free to ask.