Can anyone help me to understand how a person would be able to know when to use one version and not the other if he/she has not spend many, many hours looking over the two versions, countable and uncountable, of the word to acquire a keen sense of awareness in terms of their functionality? Is the only way to gain proficiency in this area of the English language is to develop a feeling for this type of words over a long period of time? The two definitions look amazingly similar.

The word is "feeling"

According to the Collins/Cobuild Advanced Learner's English Dictionary, a feeling, a countable noun, is an emotion, such as anger or happiness.

Feeling, an uncountable noun, is a way of thinking and reacting to things which is emotional and not planned rather than logical and practical. He was prompted to a rare outburst of feeling ... a voice that trembles with feeling.
Hey Believer...

Would you be french by any chance ? 'Cuz I don't see it any different than what you'd be faced with in french with the word 'émotion' :
COUNTABLE : Il était prompt a laisser paraitre ses émotions.
UNCOUNTABLE : Il a répondu avec de l'émotion dans la voix.
Hope this helps ?
Is the only way to gain proficiency in this area of the English language is to develop a feeling for this type these types of words over a long period of time?

Yes and no. Yes, eventually proficiency is developed by working with the language for a long time. But it may not take as long as you think. It depends on the person.

A feeling is a particular feeling, as the definition says. Anger, happiness, fear, joy -- these are all feelings. You can even have vague and nameless feelings, like the feeling that something is crawling up your back!

Feeling is emotion or passion or the fact that emotion or passion is present in some action, as the examples show. A good example is that in rehearsals in the performing arts -- music, dance, theatre -- the director may believe that the performers are not putting their hearts into the performance enough, and he will say "Once again, with feeling!", that is, with more passion, acting more involved and interested in what they are doing. He doesn't want them to have a feeling; he wants them to perform with feeling.

In general, remember that meaning is use. Google feeling, or with feeling, or the feeling, or feelings, etc., and study the use of the word in context and you will come across examples that will clarify the use of the word -- as well as examples which will make your head spin! But you can ask further questions on this forum if you get a headachy feeling!

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Thank you.

I am not French and it is hard to understand French. Is there anyway you can explain to me in English?
Sorry... I presumed you'd be french because of the title of your thread.
I wasn't really explaining the grammar point you've raised, just illustrating it with the same example in french.
I'm far from being a grammar guru and would be unable to explain this properly Emotion: embarrassed.
Hopefully someone around can... Let's wait a bit for a grammarian to pick this up !
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 CalifJim's reply was promoted to an answer.