Usually you can just slap re on the front of a word, without a hyphen, and you will be understood. There’s no need for the term to have made its way into an “authoritative” dictionary, even if there were such a thing.

There are circumstances in which the hyphen is desirable:

• if your new word with re collides with an established “re” word which has a different sense. Two of the words Carlo_R mentions are of this sort: resign and reserve.
• If you want to draw attention to the fact that you are using a “re” word in a different sense than that which would be expected, particularly if you are reverting to the base sense. “D.W.Griffith’s re-construction of the myth of the carpetbagger.”
• If you want to emphasize that you are repeating or reversing an action. “Burns opened an interesting question in 1923; but it has been completely neglected and I want to re-open it now.”

I sometimes intrude a hyphen when the word to which I’m attaching re begins with a vowel, to prevent even momentary confusion; but it’s probably not necessary.

I think John Lawler and others make a good point in that "antonyms" are vague, and I suspect that, despite the descriptivist intent, the question arises from a semantic issue.

From Wiktionary, an antonym is "a word which has the opposite meaning of another, although not necessarily in all its senses." Thus fast is an antonym of slow, but fast is also an antonym of eat. However, most of us wouldn't think about comparing speed with consumption. Useful can be interpreted as "having non-zero utility," which means the opposite of useless. However, useful can also mean "having a positive degree of utility" which is not the opposite of useless. So they are fine antonyms, but not opposite in all meanings. A more appropriate opposite for the comparative version of useful would be harmful or detrimental.

For the more descriptive questions, specifically regarding the "-ful" and "-less" suffixes, I suspect that use of these words depend on how these suffixes are commonly interpreted. "Doubtless" and "useless," for example, imply devoid of doubt and devoid of use. "Thoughtless" and "tasteless," for example, imply lacking thought and lacking taste. The latter pair would be more common in comparative relative to non-comparative use since one can be naturally seen as more or less lacking. The former pair is less commonly seen since it is less logical and descriptively less common (though not unthinkable) to be seen as more or less devoid (of course, cf. emptiest). In general the commonality of use seems to me in line with whether or not it is logical -- so I don't see them as necessarily in conflict.

However, one exception comes to my mind (not saying that there aren't others). When raukh mentioned "impossible" (p = 0), my first thought of an antonym was "certain" (p = 1). As someone more accustomed to speaking with statisticians, for me, it sounds awkward when someone says something is more or less certain. However, I recognize that both descriptively and formally, certain is a comparative adjective. Indeed, it seems that the use of certain as a comparative is more common than the use of uncertain as a comparative, although that appears to be in relative decline.

Additionally -- this is perhaps silly of me to think it needs stating -- choice of which words to use also depend upon the emphasis of the sentence, even for paired words. Whether someting is "more impossible" or "less possible" may, for some, have different connotations. Curiously, those words seem to be converging in frequency of use.