I tackled this very same problem over a decade ago and just pulled up the old file (I am very organized digitally!). It needs some updating based on what I know now, but most of your "first encounters" suggestions mirror mine to the letter, though it really depends on the person. Another good but heavier text would be "Common Ground: An Introduction To Eastern Christianity" by Pr Jordan Bajis. And for a catechism, definitely go with either Ss John Of Damascus's Exact Exposition Of The Orthodox Faith, Cyril Of Alexandria's Catechetical Lectures, or Met Hierotheos's Entering The Orthodox Church (one of the most unique and amazing catechisms); pretty much anything else (especially the convert-centric junk) is going to train the person in "bullet point Orthodoxy" and/or Orthodoxy as denomination, not the One, Holy, Catholic, Apostolic Church.
Next up would be lives of modern saints, such as Saint Seraphim Wonderworker Of Sarov by Helen Kontzevich, books about Pr Arseny, etc. The Prologue from Ochrid, the Synaxarion, and other more liturgical books are also excellent sources for saints from the more distant past. In addition to the lives, the Ladder Of Divine Ascent and The Sayings Of The Desert Fathers both communicate Orthodoxy's ascetic side in a manner very suitable to beginners and to those interested in even more ancient saints; the latter is probably one of my most-used books on this list, even to this day. And the entire Popular Patristics series is excellent, though much more targeted in scope; it is hard to go wrong with the classic writings of the saints!
Then there are plenty of books specifically targeted to conversion, all of which can be helpful: Pr Peter Gilquist's Becoming Orthodox, Pr Charles Bell's Discovering The Rich Heritage Of Orthodoxy, etc; these are more convert-centric (which is often a red flag) and light, but they can be just what some people need. I recall the online essays "12 Things I Wish I'd Known…" and Men And Church by Frederica Matthewes-Green as being pretty useful, as well as The Whole Human Person by Met Anthony Bloom and The River Of Fire by Dr Alexander Kalomiros. Stay away from blogs, with the exception of Glory To God For All Things by Pr Stephen Freeman and Pithless Thoughts by Sdn Steve Robinson; their other works (such as the radio program Our Life In Christ) and books are also very safe in general, at least compared to almost every other English-language digital primary source, though do be careful when they veer either towards "pastoralism" or "bullet point Orthodoxy" in a few odd places—neither have a solid grasp of canon law, FWIW. CS Lewis's works are also very approachable, such as The Great Divorce, and very orthodox from the perspective of a lot of modern Christianity. And then there is the interesting and seemingly-tangential How Harry Cast His Spell by John Granger, which is kind of the "key" to Lewis, Rowling, and the rest of the British Christian writers (the Inklings, etc), and really an indispensable guide to understanding the orthodox worldview more generally, which is very much opposed to mere objectivity; this is easily my *most loaned book*, so much so that I have bought about 8 copies!
I would cut Met Kallistos's works, because I just don't find them useful. Indeed, a great many innovations come from the Anglicans (especially the Oxford movement, from branch theory to "apostolic succession"). I don't ever loan his books out and I don't think they present a very solid picture of anything but Orthodoxy as *denomination*, which is not the intent but seems to be the result of that form of thinking. Maybe replace that with Orthodoxy And Heterodoxy by Pr Andrew Damick, which is flawed (from an Antiochian) but at least based on conciliar theology.
As for psalters, use the OSB (SAAS) psalter. There are so many different psalters with so many different pros and cons but what is needed now is consistency, not more noise (ie, what often happens here in "Internet Orthodoxy"). The OSB has some well-known issues (yet being well-known they're easily discussed), but having everything in *1* book is so important that it is hard to overstate. The translation is much better than almost anything you will find (not perfect, but it *works*), it uses real contemporary English (not fake old English, which has caused so many people to just walk away from Church because it is almost a foreign language to them), and the psalms are set for chanting (though calling them "metered" is a stretch).
As for prayer books, that is probably the hardest one to answer. Each of the prayer books I've used has some good points; the Sophia Press prayer book is one of the nicest, in quality, breadth, and translation (ie, real English). I actually use my own custom text (mostly based on the Jordanville, with a lot of the questionable, non-saint prayers cut, the language fixed to real English, and the OSB psalms), but there is really no "normal" prayer book because traditionally the morning and evening prayers were just doing the daily cycle (Vespers, Compline, etc). So use whatever your bishop recommends, or if there is no recommendation then just pick something that you can consistently use *every day*: a prayer book is little good when closed.
