"...about whether Mac or Win he should buy..." should be "about whether he should buy a Mac or a PC". Then the last verb in the sentence should be in past tense, since the first part of the sentence suggests this all happened in the past. "pull the trigger on it" sounds like a misheard idiom. Speakers just say something like "he went ahead and chose one."

'Hemmed and hawed' is US, so fine there. UK English it would need changing to 'hummed and hawed'. So correct and natural if you follow NA English, otherwise the small change I mentioned.

Thank you!!

It’s hummed and harred, (pronounced /hard/), in Uk English.