The following question was asked on the main site: How to pronounce 'll after ll?
Despite the question being based on something read on a book, I think that pronouncing a word ending with ll followed by a contraction of will is still possible nowadays.
Maybe people avoid saying "Jill'll come later." and prefer saying "Jill will come later." (I doubt that), but how can a English learner know that he is asking for the pronunciation of something that is rather rare to say in English?
In my opinion, questions about pronunciation are always valid, so long as the question can't be trivially answered by a dictionary.
For this reason, I'd say that questions like these are off-topic:
How do you pronounce "alumni" (off-topic, dictionary lookup)
How do you pronounce "flibberjabber"? (i.e. off-topic, since the word is not real English)
How do you pronounce "shouldn't"? (dictionary lookup)
Whereas these (in my opinion) would be on-topic:
Is n't pronounced the same in all words like shouldn't, couldn't etc? (can't be trivially solved with a dictionary)
What is the difference between "belovèd" and "beloved"? (borderline - possibly better suited to ELU, but probably also acceptable for ELL).
What is the difference in pronunciation between "cafe" and "café"? Is it the same as the difference between "rose" and "rosé"?
the person wouldn't know until they ask the question and are told that it's a rare occurrence. But even then, it's a fair question that needs to be answered. The learner wouldn't know how rare it is but at a particular point it may boggle them and make them feel insecure about whether they're using the language correctly.
