i don't think he'll retire. maybe a short break but retire? naw
i know he's frustrated because the fashion scene is what he really seems to want to pursue now but for as rich as he is, he still needs hip hop or some bridge to the hip hop to make money so that he can fund his fashion interest. the more money he speeds to get his fashion scene off the ground, the more money he needs to keep it movin'. which is why he really can't completely retire from hip hop (his "bread and butter") if he doesn't wanna go broke from takin' chances and spendin' money on fashion before he even accomplishes that goal
he even speaks on why he couldn't fully make the move into fashion in a matter of like a minute in this sway interview (at the 21:11 mark "time vs. money")
long story short; kanye is not "old" money. he needs rap or somethin' connected to the hip hop world before he retires from it and pursues fashion full time just to make sure he doesn't go broke spendin' what he does have now before he even starts to see his fashion business be successful. sure, he's rich compared to the average blue collar worker or as sly stone would say "everyday people" but kanye is "new" money
i'll say this much, his motivation and drive is unlike any other artist or entertainer right now