1. Quello è l'uomo che compra IL caffè DA Rao's Coffee. You can use also "PRENDE IL CAFFE" , not "COMPRA" 2. Quello è l'uomo che prende il caffè da Rao's Coffee It's a tipical italian grammar costruction, like in english "make a cake" or "take a bus"

1) use of "DA" and "AL" sometimes could be controversial. Examples: "A colazione solitamente prendo un caffè AL bar" is right. "DAL bar" is wrong. I'm not a teacher and I can't help you with a rule.... but when speaking about bar in general it is rightfor sure. Your translation"Quello è l'uomo che prende il caffè DA Rao's Coffe" is right... but "AL Rao's Coffee" could be used too. Keep in mind that "AL" in this context is used to point out a place. "DA" in this context is used to tranlsate your english sentences "take something from someone/somewhere". 2) when speaking about coffee in general you must use "il caffè" (singolare)