I so wish I could help, but I don't think there is an "order of reading" ... unless I could say that Fr. Seraphim's book MIGHT have been helpful before Theodora. Theodora is just something that can cause huge confusion, if you've read it? I think it's best to hold off on that until after all one's questions have been answered and one is comfortable in the understanding. And maybe not even then.
The quotes from the liturgical hymns and all don't say much. Only that essentially we should be concerned about our souls after death, and that we can expect attacks from demons, trials, etc. When information is brief like that, we tend to read into it to confirm what we've already heard/understand. (I think a little like people will find confirmation of whatever they've already been taught by reading isolated verses of Scripture, so that different denominations all feel justified in their arguments.) So I think it's better to have it all EXPLAINED to us before we get those isolated bits. And we don't want Theodora being our explanation because it causes a lot of confusion (in my case at least). And it's not easy to forget it so that we can relearn something more moderate.
I listened to probably every podcast on AFR about the soul after death. A few of them outright dismissed tollhouses - sometimes completely in reaction to Throdora. But then overall they still explained the process of the demons attempting to tempt or deceive or frighten or cause the soul to despair (I suspect the demons are clever enough to know exactly what is most likely to work on each of us) ... and the help of angels (which oddly seem to often not appear quite as quickly as the demons sometimes - so if that were to happen, I fear for the conclusions a soul might reach who was very convinced of the evangelical/Protestant understanding I was brought up with - that could be terror and despair and crumbling of the faith of one who considered himself in Christ who assumed he would be immediately whisked to heaven with no intermediary state).
And I asked questions here. Often the answers revolved around "don't take it too literally" but to be honest, for me it took time to discover what that meant. But when I'd ask something more specific, as you've been doing, the answers helped little by little, each one like a single brick in a wall being slowly built.
By the time I read Fr. Seraphim, I think I pretty much had it sorted out. So it was a great comfort to me. He spends several chapters (iirc) explaining little bits of the overall understanding and especially comparing them with NDEs, so that's another aspect that helps. So many kinds of beliefs available, and when we layer them and point out what's true and what's not (compare and contrast) it helps to zero in on the truth.
I think the podcasts on AFR were overall helpful but they didn't speak with a single voice. It was again, bits I had to put together into an overall context. I can look for those episodes (and in some cases, series) if you like? But I doubt I'd have time to re-listen and comment on specifically how they fit in overall. But if you bring specific questions here, I imagine Fr Matt or someone can help? I would try.
Maybe if we had a catechetical book "read this first before reading anything else" it might help. I don't know. People are too easily fascinated with this topic, and silly discussions happen in some places (Facebook anyone?
) and then things like Theodora can produce massive confusion. Within all that, some things needs to be torn down before truth can take root. I was a victim of that. An my priest told me not to study/read certain things ... and I think he was right, and in fact I avoided those books and topics. But it's out there (often misinformed) and we get exposed to it so SOME opinion will form. Because of the world we are in (especially online) ... maybe it's better to lay it out simply for converts? I don't know. Typical wisdom is to avoid the Ladder, avoid tollhouses, etc. Who am I to question the priests? But I fell through the cracks as a result, and I can see MANY people do (witness all the errors in discussions online) so ...
We need a sane voice teaching us at some point.
AFR, and questions here in CF, and then Fr. Seraphim's book were the steps in that order that helped me at least. Problem was other things I read first (especially Theodora and FB comments) muddied the water SO much initially.
If that helps?