I believe he will retire off and on, and might fight on to deep in his 50's against easy targets like MMA guys making their boxing debut. ...that's what you meant right?!
I think it depends on his investments. We all know he spends a lot and mayweather promotions hasn't had any ppv quality events. If he blows his money-he'll be back
Yes, he better be wise with his earnings. If he go on he will meet his Tarver. Roy made mistake after won a belt at heavy to drop down to fight a top challenger in Tarver. He should have retired or try to get a fight with Tyson or Holy. Floyd is eerie to make the same mistake, which is why he retires after every big fight. If he doesn't need the money, he can pick and choose.