[NoOne]

if it's a true superstar you are odds on better off signing him now than waiting a year or 2. he wins another mvp or just has some good seasons and it goes up to max cost relative to his ratings.

if you think he's gotten lucky and should regress a bit, you wait for that better contract.

based on what you've stated, i'd lean toward signing him now as opposed to later.

heh, i stopped doing my awards asap in offseason due to awards messing up my contract extensions. i kept having an odd player on occasion not signing a previously accepted offer. it was often a younger player taking a deal early in arb years and also winning an MVP or something -- since nothing else seemed to change in the equation over the course of those few days, i am assuming that is the cause. between saying yes and winning that award they had not completed the contract extension. they win the award and think they deserve more.

i make sure arb deals are signed before doing awards, if possible. just one more thing that can escalate salary.

"too early" all depends on context. you neglect to sign them to an extension in year 3 and they aren't receptive in year 4. it's a bit of a risk to try to maximize this stuff. my main concern is their age and how long the term is. trading a guy signed to 33 is easier than a guy signed until 35 and you get a better return. also, i'd rather they not age on my team... again, greater returns. signed to ~33 at latest and not likely to be on my team after ~29-32 anyway. so, for me at least, extending them at or before age ~25-27 is key. what # year they are in of club control is less significant.

heck, if they will be ~30+ after 7 years, i won't even bother extending in many circumstances. they simply won't be around long enough to bother. destined for comp pick or trade for sure... too old to build around with confidence @2nd contract, imo.

edit: i have no idea if something is off above -- something screwed up while editing and i don't feel like proof-reading, lol.... other note i wanted to add:

it mostly evens out whether you extend in year 1-X. you get less of a deal in year 7 since you aren't buying any arb years. the difference between arb values and average salary of extension all jive with each other. yeah it costs a bit more the next year, but you aren't buying out a "cheaper" year... relative to arb costs, you are basically paying the same amount and just redistributing it.

mix a few arb years with FA costs and you get an extension average. you only "lost" if you needed the money spread out. you may have even benefited by paying the lower arb cost and waiting a year as costs drop the following year etc etc....