Yeah, I don't know if loser is harsher in some places than others; here (mid UK) it's moderately mild, but the US might be different, for example. Roan is supposed to straddle that line between almost being too much of an asshole - sorry if it didn't work for you.
3 year old comment, but I thought I may as well add it here - I found the use of the word, 'loser' a bit much as well. While in New Zealand its not really that bad a word, it just jarred too badly for me that I had to stop playing Roan's route. Which was really disappointing. I didn't mind the asshole part - but something about the use of that word just didn't land for me - I think being called a, 'bitch' would have landed less offensively for some reason.