Plebes normally get no say around roommate assignments. I didn't get to pick my roommate until I was a firstie, but I assume that may have changed as I attended West Point in the last century.
DS is a firstie and says it is company dependent. He has always been able to preference, including 2nd semester plebe. By the time you’re a firstie, one of your buddies is usually in charge of assigning rooms and knows who wants to be roommates. Mine has been lucky and has had a 2 man room for the last 2 years.
definitely company/TAC team dependent. I did not get to pick my roommates during plebe year. Got to pick roommates the rest of the 3 years. keep in mind that just because you are good friends with someone, it doesnt mean that you two will be great roommates