There's a common exception to the "An for nouns beginning with vowels, A for nouns beginning with consonants" which is "if the first vowel makes a Y sound, treat is as a consonant."

Because it's pronounced ˈjʊə.ɹəp, the first sound is a soft j not one of the 5 vowels (a,e,i,o,u) and it's only the pronunciation, not the speelling that determines the choice of an/a

The rule is that “a” goes before a word starting with a consonant. And “an" goes before a word starting with a vowel.

BUT the rules follows the phonetic pronunciation NOT the spelling.

some examples with pronunciation in [brackets]

"a" + consonant (both in spelling and pronunciation)

• a cat [k]
• a dog [d]
• a purple onion [p]
• a buffalo [b]
• a big apple [b]

"a" + vowel that is pronounced like a consonant

• a European [ˌjʊɚ...] say: a juropean
• a one-legged man [ˈwan] say: a won-legged man
• a union [ˈjuːn.jən] say: a junion)

"an" + vowel (both in spelling and pronunciation)

• an apricot
• an egg
• an orbit
• an uprising

"an" before consonant that is pronounced like w vowel

• an honorable person [ˈɒnəɹəbl̩] say: an onorable person)
• an honest error [ˈɒnɪst] say: an onest error

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It'll blow your mind when you discover how words like umpire, apron & uncle were originally numpire, napon and nuncle; so a numpire, a napron and a nuncle.

I believe the process of how they became how they are today is called rebracketing.

I think you are right. An umbrella is a useful tool. Uh sound vs you sound is what makes the shift.

I say eye-tem, not eee-tem for the word item. But it is still an eyeball or an emotion.