This is the 1st time I've tried out a challenge, and its definitely living up to its name! I'm now in my 2019-2020 season, and have yet to make the playoffs. I've been finding playing the game normally without any limitations to be too easy and gets boring before long, so playing with the challenge rules definitely adds to the fun.
I finished the previous seasons with the following records:
2015-16: 76pts (36-42-4)
2016-17: 79pts (35-38-9)
2017-18: 78pts (34-38-10)
2018-19: 89pts (38-31-3)
Things are looking way, waaaay up now, though. I'm 17 games into the season with a 14-1-2 record! I guess I'm excited enough about this hot start to post on these forums for the 1st time in years, so here are some of the key things over the seasons that got me here (ie. the big trades and the draft picks that have made any impact at the NHL level/look like they will make an impact*):
2015-16 Key Trades:
Antti Niemi, Matt D'Agostini, Mike Kostka for Andrei Vasilevsky (TB)
Joe Pavelski, Marc-Edouard Vlasic, Brent Burns for Gabriel Landeskog (COL)
Joe Thornton for WPG 1st round pick
Patrick Marleau for Austin Watson (NSH)
2016 Key Draft Picks:
Round 1 - 6th overall - Logan Brown
Round 1 - 21st overall - Luke Green
Round 2 - 36th overall - Chad Krys
2016-17 Key Trades:
Logan Couture, Erik Johnson for Zemgus Girgensons, Jake McCabe (BUF)
Alex Stalock, Ben Smith, Eriah Hayes for Sean Couturier (PHI), CBJ 2nd round pick
Tommy Wingels for Anthony DeAngelo (TB), TB 3rd round pick
Matt Nieto for Robby Fabri (STL)
2017 Key Draft Picks:
Round 1 - 7th overall - Antoine Crete-Belzile*
Round 2 - 38th overall - Colton Scott*
Round 2 - 46th overall - Reid Weller*
Round 7 - 188th overall - Grant Randall*
2017-18 Key Trades:
Sean Couturier for Juuse Saaros (NSH), MTL 4th round pick
Daniil Tarasov, Melker Karlsson for CHI 1st round pick, CHI 4th round pick, CHI 5th round pick, CHI 6th round pick, CHI 7th round pick
2018 Key Draft Picks:
Round 1 - 1st overall - Joseph Veleno (I finished 7th last, lottery luck at the perfect time!)
Round 1 - 21st overall - Oliver Walhstrom*
Round 2 - 36th overall - Karl-Anton Ahlstrand*
Round 2 - 52nd overall - Gabriel Olsson Frommel*
Round 3- 66th overall - David Jonsson
Round 3 - 76th overall - Jayson Montgomery*
Round 4 - 96th overall - Ivan Khomenko*
Round 6 - 171st overall - Ian Blacker*
Round 7 - 201st overall - Kirk Rushmer
2018-19 Trades:
Dylan Demelo for Rasmus Ristolainen (BUF)
2019 Key Draft Picks:
Round 1 - 14th overall - Rickard Nordin*
Still too close to this draft to have a good idea of who might make the NHL, so these are just the rest of my picks:
Round 2 - 44th overall - Remi Lamoureux
Round 2 - 48th overall - Will Lucia
Round 3 - 63rd overall - Spencer Desbiens
Round 3 - 74th overall - Sten-Allan Stahl
Round 4 - 104th overall - Harrison Blaisdell
Round 5 - 134 overall - Jerrycko Manning
Round 6 - 164th overall - Juraj Sisak
Round 7 - 194th overall - Rickard Hollstrom
2019-20 Key Trades (so far):
Gabriel Landeskog for Auston Matthews (FLA) (I tried to re-sign Landeskog pre-season since he would be UFA at season's end but even at 50mil/5yrs he wouldn't sign, so since he was older than 26 out the door he went!)
Current coaching staff:
Guy Boucher (Head Coach)
Joel Otto
Mike Pelino
Sam St. Laurent
Alain Vigneault
Mike Babcock
Current Lines (* denotes rookies):
Forwards:
Tomas Hertl - Auston Matthews - Nikolai Goldobin
Zemgus Girgensons - Joseph Veleno* - Travis Konecny
Jake DeBrusk - Austin Watson - David Jonsson
Robby Fabri - Logan Brown* - Ryan Hartman
Defense:
Chad Krys - Luke Green
Mirco Muller - Anthony DeAngelo
Jake McCabe - Rasmus Ristolainen
Goaltenders:
Andrei Vasilevsky
Juuse Saaros
I'm doing this challenge more out of fun for myself and don't plan on submitting it, so while I hope that I've managed to stick to the rules of the challenge, if you notice anything that slips outside of that then, 1st: my bad!, and 2nd: no worries this won't be up for official consideration anyway

I plan on carrying on with this game beyond 5 seasons and have added a couple of new rules for myself. First, I plan to keep the min player age of someone that can be traded at 25 (ie. the trading age stops lowering at 25, then can never trade anyone under 25). Second, I am going to
slightly relax the no trading of draft picks rule so that I can make ONE trade involving draft picks, and it has to be at the draft, and can either be multiple picks packaged for a higher pick (ie. I trade a pair of 2nd rounders for a 1st rounder) OR a pick thrown into a trade (but only in a trade involving a 25+ year old player leaving my team.)