Phrase ‘A Bottle of Water’ in Native English – Word Usage

These are all meaningful, but the meaning is changed and the context in which they could be used would be changed. "Would" is more often used to discuss expectations (that one feels certain about) in projected courses of action, rather than hopes or expectations in the current situation. You wouldn't use "would" there except in limited circumstances, when you are very confident in your predictions. I think a lot of this falls out of the use of "should" to describe model behavior or what is 'right' (like def. 3 here). Incidentally, I think (without proof) that that is why we don't use "should" to describe expectations that go awry, like the train being late: we certainly don't think that our hopes or expectations ought to be denied!

1. with "should" is a prediction; with "would" the speaker is certain enough to, for instance, discount the possibility of it not having been received. ("They would have it by now, so that can't be the reason they haven't responded...")

2. "should" states a probable expectation, while "would" is more like a certainty in a hypothetical plan ("We would get there by six, which would give us time to change before dinner...")

3. is tough. "We wouldn't have to wait much longer" is an acceptable utterance with an appropriate context: if I'm making a case for my plan (staying in line) over your plan (leaving the line). The implied full thought is "we wouldn't have to wait much longer [if we agreed to stay]." Here we are discussing the expected-to-be-certain details of possible plans, rather than stating our hopes about the future.

4. would work if you'd said "there were no reports of delays, the train would be on time [and that is why I am worried that your sister hasn't arrived yet]". This is related to sentence 1; I am stating a prediction about which I feel certain enough that I discount the train being late as a possible reason that your sister is delayed, and start worrying that something else could have happened to her.

5. Meaning is completely changed--we don't use "should" to emphasize things that happen contrary to expectation. Sometimes "The train would be late!" (with emphasis) is used expressing frustration that the train is late. The resulting statement is whining. A more full example: "The train would be late on the day I have an interview! This always happens to me!"

So: the distinction as I see it is pretty much what your edited addition says. "Should" suggests a more tentative attitude than "would," which may be from genuine uncertainty, or from an attempt to be more polite or more emotionally removed.

Both "should" and "would" are used to discuss an event about which the speaker is not completely certain or confident. But "would" seems to have the implication of talking about the details of a hypothetical world, future course of action, proposed plan, etc. "Should" is used to make less confident predictions about the future.

If you check the entry for of on Wordnik, you’ll find:

Before; until: five minutes of two.

Therefore, I’d regard the phrasing you ask about to be grammatical. However, I don’t generally hear that wording used with the fraction quarter. As said in the comments, phrases like:

• quarter to four
• fifteen minutes before four

are more common.

As for whether this person was using that phrasing to be humorous, you’d have to ask your friend. It might be colloquial.