boQwI' gives you an option of using k -> {q} or {Q}, is that something feasible on your end?

I prefer to use boQwI' with k -> {Q}, since I can just use q for {q}. But I have noticed that some fonts use k for {q} and q for {Q} (or, technically, they use K for {q} and Q for {Q}, since the fonts map pIqaD to capital letters). I think I might be in the minority on this one.

I prefer k -> q. In transliteration, k that isn't part of a cluster nearly always ends up as q, while kr tends to be the transliteration of Q. Since native English speakers consider k simpler than consonant clusters of k, and since k is more common than q, and q is odd to an English speaker with a following u, I think k is more suitable for q. It's just a bias for an arbitrary choice though, not a logical argument for it.

(Obviously, we should ask Okrand to make a ruling one way or another, just to sort it out.)

A ruling on what? Okrand isn't in charge of keyboard mappings or anything like that; he isn't even in charge of what Klingon LOOKS like. All he knows is what Maltz tells him, and Maltz will just say Klingon computers already have pIqaD on them, so there's no mapping issue.

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SuStel
http://trimboli.name