Thanks for the list. A mixed bag, many unanswered p-- or answered badly -- some even great, all good to look at. S0, (says he as inevitably as death in Texas)
Don't knock worry about armadillos, they may not be great questions but the are real -- and usually solvable. And sometimes they bring good things to light: look at kinkajous!
Scope of 'ala' A great one, usually dealt with by "context will tell." But it often doesn't and it makes for real problems when there are quantifiers or conjunctions around and we have to work out how many whatsis do what or not. There are some clear cases (second word after 'pi', for one) but after that it is all variable at some level.
Canonical. What Sonja says (too seldom, alas, and not a lot lately), what Pije said generally, what others have said and not been successfully challenged on, what someone can argue for until the opposition gives up. (no names). Oh, and the latest version of Setepo's PSG, though that is known to be incomplete and occasionally inaccurate. Preetty much answered and yet fairly important still
The "right" metaphors for abstractions. "There are nine and ninety ways of writing tribal lays and every single one of them is right" (Kipling) Ditto for metaphors for whatever. It would be nice to come up with coherent patterns and that without just copying English or Swahili or whatever, but what we really need is some decisions, rather than wandering around, each following his own light. I like 'pini' and 'kama' and maybe 'awen' for time, but that is just my light and others have spatial or some other sorts of metaphors. Let's decide (or get a bull from Sonja). Unanswered and at least moderately great
Reduplication. By law, as it were, two adjoining content words are modificand and modifier. In the case of 'wile wile' we don't really have that but close enough that we can say "there is a change of realm here" "need to want" or some such. For 'kala kala' we know it will depend on context and we can even imagine various contexts for it: to distinguish "real" fish from whales and lobsters and whatever else may be counted as kala, for example.
Limits of loan words. So far it is supposedly clear (but rapidly being violated) that these are proper names and that they can enter only as adjectives to tp nouns. This seems to me to be failing fast: I expect that 'suwi pimeja Mesiko' is accepted in place of 'suwi pimeja pi ma Mesiko' even though the chocolate bar is not called "Mexico."
And it appears that quoted expressions are rapidly losing their 'nimi ni' (though that may be a different phenomenon). Whether this is a disaster or just an inevitable evolutionary step, I don't know, but it does open doors that we may not want to open, certainly not inadvertently. So, great, though officially answered. Some how, kulupu sona pi toki pona doesn't look like a real contender for a functioning group.
Punctuation. Probably trivial, but interesting anyhow. We want 1) to reproduce in writing some of the information that is given in speech by non segmental phonic effects. Now, in tp most of the major such places are already covered by explicit words (la, li, e). The most obvious one that is not -- and that creates problems -- is the final prep phrase(s), which might usefully be set off by a comma, at least some times. The others, like the end of 'pi' constructions and the scope of following modifiers seem to complex to deal with (no good device exists except parens and we just aren't going to use them at a bet -- we often don't really know or care where the scope really is). As for quotes, well, they are officially proper adjectives (modifying 'nimi' or the like) but, as noted, that connection is weak. I suppose we will continue to use quotes so long as there is someone with only a fixed font keyboard. As for other things one might want to do, stress has 'kin,' though not reliably, and then we fall back on all those other characters: caps, itals, bold and underline (etc., depending on the resources of your program).
Spelling. Well we need words for the letters (but of what alphabet after all?) for the same reason we need names for the numerals: for addresses and the like. Presumably, these can be used for spelling as well -- though spelling bee in tp are not going to be very interesting. Unanswered yet, but minor.
tenpo 22 li kama. mi wile lape. tenpo suno kama mi awen sitelen e ijo pi toki ni