I guess a lot would depend where the Jets are 3 years from now. Wheeler will be 33 y/o at the end of his current contract and if the Jets have become a contender or on the verge with a bunch of young stars he may be content to sign on for 2-3 more years at a fair price. 33 is a bit on the high side to get the 5-7 year big ticket contract as a UFA. Ladd was 30 and pushing it.
I think by the time we have to discuss Wheeler's re-signing the league will have fully established that you get the big bucks in your twenties, not your thirties. Teams will really be seeing the liabilities that these older guys are on their 5-6-7th years into their deals at $6+ million and a cap that isn't cooperating by going up.
Going forward in the NHL I expect that guys will sign a 6-7-8 year deal coming out of their ELC. If they do it from a self-interest standpoint they'll sign for six, meaning they'll be in the range of 21-24 when they sign it, 27-30 when they're due for their next deal. If you're on the young side of the range you'll see another 6-7 year deal and if you're on the higher end, you'll be looking at 3-4 years and probably less money.
30 will be old. 33 is ancient. 35 is retirement. Wheeler's decision will be based on his comfort in staying in the city and whether the team gives him a shot at a cup.