Reddit mentions of Samurai Swordmanship Vol. 1: Basic Sword Program by Masayuki Shimabukuro

Hi there. I applaud your interest in traditional JSA (Japanese Sword Arts). I am not at all an expert but I did study Nakamura Ryū for two years. First, a quick and small correction: iaitō = sword for iai, iaidō = the way of iai.

The standard, default advice you will get on this matter, as with any kind of combat skill or physical activity, is this:

Get a qualified teacher.

Yes, you can begin "studying" with a bokken and not risk injury quite as much as with an iaitō or shinken (live blade), but you will invariably develop some bad habits that will be very difficult to unlearn. Better to start your journey with a clean slate if possible. All the books and videos that exist cannot critique your form and mistakes, or show you in-person the right way to do it, or explain things you are not picking up on. And moving up to shinken without training is a bad idea, for obvious reasons I hope.

To that end, the folks at e-Budo* can help you find a legitimate JSA dōjō near you, if one exists. Note that "near you" is a relative term; some iaidōka travel hours to get to practice. That is the exception rather than the rule, I'm just pointing out that people make it work if they really want it.

With all that being said…

I didn't read many iai books when I was studying Nakamura Ryū — I was always much more interested in the art historical aspects of the arms & armor, not as much the usage — but I know that Flashing Steel is a popular book about a legitimate style (Muso Jikiden Eishin Ryū). The same author also produced a video series which I have never seen. Of course I would be remiss if I did not mention my own ryū's founder, Nakamura Taizaburo, and his book on the subject.

These books will not allow you to "learn iaidō" in a practical sense, but they will give you a solid start on understanding it, studying the fundamentals in an academic way, etc. I mean, you can of course pick up a lot of practical skills… but you will also be interpreting the instruction in a unique way, and the result will not be correct from the school's perspective. This is the kind of difficulty that WMA (Western Martial Arts) practitioners face, interpreting historic fencing manuals… if they had the option, you can bet they'd study under living inheritors of those styles.

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*Unfortunately e-Budo seems to be stalling at this moment.

I've read enough to know it's not worth buying. But I'm talking about this garbage:

https://www.amazon.com/Samurai-Swordmanship-Vol-Masayuki-Shimabukuro/dp/B0017TCSLW