IDK I think it becomes a real problem at year 9 when all of a sudden you're looking at paying 35% for Jaylen Brown after he made an All-NBA 2nd team and you're in a damned if you do, damned if you don't situation. So third contract is when you're having to make really tough decisions. Second one you're probably thrilled to pay a 30% max deal if your 24 year old guy has made All NBA, won MVP, won DPOY, etc to qualify for that supermax. If they're at 25% max salaries meh, Vassell makes 83% of a 25% max right now.