Learn English – Why is “union” an exception to the “a/an” rule?

What about "not that high (of) a fence"? "not that red (of) a heart" "not that smart (of) a person? not that big (of) a problem?

I would argue that if you use the word that to qualify the adjective, the of conveys the meaning of comparison of a specific entity to the class of general entities to which it belongs.

I'm sure the usage can be regional, as well. There is no hard and fast rule.

EDIT

Hey, I did some more research. Dictionary.com has the following usage note for "of" :

Of is sometimes added to phrases beginning with the adverb how or too followed by a descriptive adjective: How long of a drive will it be? It's too hot of a day for tennis. This construction is probably modeled on that in which how or too is followed by much, an unquestionably standard use in all varieties of speech and writing: How much of a problem will that cause the government? There was too much of an uproar for the speaker to be heard. The use of of with descriptive adjectives after how or too is largely restricted to informal speech. It occurs occasionally in informal writing and written representations of speech.

So, I suppose that's the reason why adjectives other than "much" combined with "of" sound odd to your ear. I believe "that" can be included with "how" or "too" in this synopsis. Replacing "much" with another adjective occurs occasionally in informal writing and in speech, but isn't unquestionably standard.

When I say these constructions out loud, to me, I often want to insert the of but perhaps that has something more to say about the informality of my speech rather than the correctness of the construction. :)

In your sentence as amended, send is without a doubt in the present indicative tense (and it is not a conditional sentence). In English, however, the present tense does rather more than express what’s going on in the present. To talk about something that’s going on right now, we generally use be + the –ing form of the verb which describes the action or state. We use the present tense, on the other hand, to refer to:

(1) a fact that is always or generally true (Water boils at 100 degrees centigrade);

(2) a repeated action (I go to church every Sunday);

(3) an event that occurs at the moment we are speaking (I promise); and

(4) fixed or planned events taking place in the future (My flight leaves early tomorrow morning).

In your example, send could express either (2) or (4), depending on the context. In either case, it is understood that the schedules are or will be sent according to a pre-arranged plan. If that were not to be the case, you would have to say We might be able to figure this out from the schedules you’ll be sending us. Perhaps that was what your boss meant. If so, he was half right, but we express the future by using will + the plain form of the verb only when we are making a prediction or when we are expressing a decision, often made at the time of speaking, about the immediate future. Neither of those cases seems likely given the first half of the sentence.