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1) if there are any special changes in pronunciation before personal pronouns with the 1st Conjugation -adh endings (as is the case with some future and conditional tense endings?…
Such as (A) luascfaidh [LOOSK.hee] will rock, but Luascfaidh mé (LOOSK.huh māy) I will rock.
And (B) luascfadh (LOOSK.hoo) would rock, but Luascfadh sé (LOOSK.hutt shāy) He would rock.
Right except that -ua- is pronounced oo-ah in Ulster, so : LOO-ah-skee, etc.
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Or is the past habitual always “oo” (Luascadh mé, sé, etc. = LOOSK.oo māy, shāy, etc.)
It works like the conditional, but be careful, the endings are luascainn, luascthá, luascadh sé (Loo-ah-skutt shah...).
Note : when unstressed (ie. most of the time), the personal pronouns don't have long vowels and their vowel may change a bit: mé [mah], sé [shah], siad [shuh-d]
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2) I found an old BBC article saying that, similarly to 2nd conjugation future/conditional tense endings, past habitual endings are pronounced multi-syllabically in Ulster (I’m assuming that the writer was probably only referring exclusively to 2nd (not 1st) Conjugation, 3rd Person Sing. Past Habitual Verbs?)…however he only stated that their pronunciation is “a quare handlin’” and then gave a way to avoid using the past habitual with the “Ba gnáth le…” format, but he never did say how the multi-syllabic past habitual is pronounced. Is it something like…
Cheannaíodh (HYANN.ee.aw.hoo), often bought
and… Cheannaíodh sé (HYANN.ee.aw.huh shāy), He often bought. ??
Should bee HYANN-ee-oo before any subject except personal pronouns.
Cheannaíodh sé would be "HYANN-eett-shah".
But in most of Donegal (especially in the North), many endings with a long -í- are shortened and people actually say "cheannadh", "cheannainn"...
Also, and it might make you feel you've been wasting your time

, nowadays and for decades now, Donegal speakers use the conditional instead of the past habitual, or "ba ghnách" + verbal noun phrase.
I used to go fishing = Rachainn a dh'iascaireacht, or: Ba ghnách liom ghabháil a dh'iascaireacht.
I can ask native speakers on Facebook to be sure but I think the past habitual is rather a literary form that people don't use in speech (in Donegal - it's alive elsewhere, I think).