More out of curiosity but looking at some players who signed past 35+ in the last decade or so:
Whitney signed a 35+ contract for 130% of his highest cap prior (which in turn was a 35+ contract)
Williams signed a 35+ contract for 120% of his highest cap prior
Thornton signed a 35+ contract for 115% of his highest cap prior
Datsyuk signed a 35+ contract for 110% of his highest cap prior
Gonchar signed a 35+ contract for 110% of his highest cap prior
St. Louis signed a 35+ contract for 105% of his highest cap prior
Markov signed a 35+ contract for 100% of his highest cap prior
Ovechkin signed a 35+ contract for 100% of his highest cap prior
Alfredsson signed a 35+ contract for 100% of his highest cap prior
Kovalchuk signed a 35+ contract for 95% of his highest cap prior
Timonen signed a 35+ contract for 95% of his highest cap prior
Doan signed a 35+ contract for 90% of his highest cap prior
Elias signed a 35+ contract for 90% of his highest cap prior
Chara signed a 35+ contract for 90% of his highest cap prior
Pavelski signed a 35+ contract for 85% of his highest cap prior
Visnovsky signed a 35+ contract for 85% of his highest cap prior
Koivu signed a 35+ contract for 80% of his highest cap prior
Bieksa signed a 35+ contract for 85% of his highest cap prior
Iginla signed a 35+ contract for 85% of his highest cap prior
Pronger signed a 35+ contract for 80% of his highest cap prior (and with bonus years...)
Some of them multiple years, some of them bonus laden. Malkin will be added to the list shortly.
Inversely Spezza and Parise signed 35+ contracts for 10% of their highest cap, and many many many more players never play past 35.
Gaudreau is an elite player without injury history and elite players tend to be able to perform at high levels for longer. However, he isn't known for being a fitness freak like many of those players listed who still remain big and strong when they age, but Kane is about to be 34 and still performing at elite levels. Of course he loses guaranteed income with signing a smaller total value 7 year contract than an 8, but I highly doubt his agent is telling him that he should be assuming that 8 year is worth $0 if he signs a 7 year contract (and if it is, that's not good for a team signing him to 8 years lol).
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