Second question - What did you expect? He's a career criminal with mafia ties. You expected for him to sit back and retire at a rather young age for a criminal? It's their mentality, it's in their blood. Either you go in fully, or you don't go in at all(at least when it's the case of blue collar criminals).
But still, after his first drug sentence Madonna could have switched to other kinds of crime; for example, Salvatore Santoro (who later became Lucchese underboss) did time for drugs, but after getting out switched to labor racketeering I think and wasn't involved in drugs anymore.
Instead, Madonna made twice the same mistake.
