"wesleyabridle
I say the hyphens are over used here. We are progressing away from Latin, not regressing back."

What are you talking about? Hyphens were not used in Latin at all. Heck, the Romans did not even use spaces between words! What would they have wanted hyphens for?

And in what sense are we " progressing away from Latin"? Language development is not progressive. (And English did not develop from Latin, not mainly, anyway.)

Anyway, I agree with those who say we need two hyphens: "five-year-olds."

I have a floccinaucinihilipilification of the use of "floccinaucinihilipilification" in conversation.

Actually, the “of a” construction seems better to me in these cases. I am not sure why, but somehow the “of” seems to indicate that temporal rather than spatial extension is being talked about: I would not say, or write, “How long of a piece of string is it?” However, when I read “How long a process is it?” (without “of”), I feel myself hesitate momentarily between the more common temporal sense of “length of a process” and the less common spatial sense. The “of” seems to remove that ambiguity, making the meaning clearly temporal, and the sentence thus flows better with it there.

I have been told the shortest English sentence is actually "Go!" (It is an imperative, and the subject "you" is implied.)

"I am" is shorter than "It is."

I am fine with "Fine."

What about "No"?

I do not think I have ever heard (much less read) people using THAT in the way that you say.

“I wonder THAT this is correct” does not mean the same thing as “I wonder IF (or WHETHER) this is correct”, it is a rather awkward way of saying something like "I am (or will be) amazed to find that this is correct."

According to the OED, “perpendicular” has been used to mean “at right angles” since at least c1475 (and their earliest sighting of it used to mean “vertical” is only 25 years earlier). This usage is not new by any stretch of the imagination. The dictionary does say, however, that it is found “chiefly” in science and engineering (presumably including mathematics). Perhaps it is finding it used outside of this context that is bothering you.

Just because a certain suffix, when added to another word, modifies the meaning of that word in a predictable way, it does not follow that you can add that suffix to any old word whose meaning you might happen to want to modify in that way, and expect what you say or write to be accepted as standard, idiomatic English, or even necessarily be readily understood.

It is not a matter of types of words; it is a matter of particular words for which the suffix has become established as a standard modification. It is not a question of grammar, but of idiom.

“Homeward” (and “homewards”) are established English words. So, I think, is “sunward,” though it is a lot less common. However, “Jerusalemwards” and “flameward” are not established English words (and neither are most other compounds you could make this way). If you use them, your audience will be confused. They may be able to figure out the intended meaning in a moment or two, but they will probably suspect that you are either not a native speaker, or that you are making some sort of linguistic joke.

The same goes for “unswimworthy”, “unwatchworthy” and “unbuyworthy” (or, come to that “swimworthy”, “watchworthy” and “buyworthy”). They are not standard or idiomatic English, and although native speakers may not find them incomprehensible, they probably will find them confusing and weird.