I'll say this, with the caveat that I never did finish the book due to unrelated reasons, this is an excellent method.

One may think "It's fine, I'll simply read the text and then, if I have questions, absorb some scholarly articles on it." Trust me, you will enjoy it so much more when you understand Joyce's intent and clever writing as it happens. You simply can't take it all in post-factum, too much would be missed.

There also is https://www.ulyssesguide.com. It has episode guides, which explain what actually happens in each chapter (this can sometimes be difficult to decifer), the cross references to other chapters, and sometimes possible interpretations. I found that extremely helpful and would have missed a ton without even noticing.

Thanks for the link, this does make it more approachable!

Something like this but for The Iliad would be awesome

The Iliad is much more approachable with a background in ancient history. Whereas I feel only a background in Ulysses really helps with Ulysses.

Is the effort worth it?

If you're a fan of modernist literature or of literature as an at form, undoubtedly yes. If you're just interested in reading it because it is (justifiably, in my opinion) famous, then possibly.

It's a bit like reading and studying the Bible if you're not religious. Will you come out having read and studied one of the foundational texts in English literature, able to approach later texts with fresh eyes to the unending allusions it spawned? Yep. Will it be 'worth it', though, in a revelatory sense? That's up to you in the end.

It's certainly worth it, especially if you have some appreciation for the craft of writing, a love for words and the English language and the patience to take things slow and put the effort to really understand what you're reading. After the clouds clear and you can see what he is doing a monument reveals itself and there is this feeling of astonishment that a human was able to create such a thing.

The second half of the book (chapters 10 to 18 although page-wise it's more like two thirds) is especially satisfying. Each chapter is written in a vastly different style: imitation of music, a romantic novel, a play, the historical development of style in the English language, how a bad writer writes, a technical text, and a couple of others.

It's challenging and might not be satisfying if you're looking for plot (there is none). I suggest to read a chapter and then the accompanying text in https://www.ulyssesguide.com