By the way, how did you hold the checkpoint Spronk? Did you just stay in VoG as the reset happened? I wasn't sure if that would work but considered trying it...
I stayed in a VOG HM checkpoint at 2am (as long as you are logged in before 2am all your checkpoints are from last week) and a friend closed the game, restarted it, and joined my fireteam. he verified he was "clear" by seeing that his nightfall icon at the start screen was clear after he reset his game. Once he was inside my VOG hm save, i shut my game down, restarted it, and joined him.
Doing it solo isn't enough, another person on reddit tried being inside his own during the 2am reset and then restarting the game, but with 2 (or more) people you can roll checkpoints over week to week. after that we just juggled our alts inside that HM checkpoint until we had 3 chars each with the save.
if anyone needs the save i'm up now but out to walk my dog for a bit, no patch yet
re: crucible loot is completely independent of performance. a win nets you 25 rep and 3 marks, and a loss nets you 10 rep and 2 marks. so the difference is trivial, doesn't really matter win or lose. there is one bounty that asks you to win 3 crucibles so thats the only time it sorta matters. also iron banner gives you 25 rep for a win and 0 rep for a loss so you see people quitting the second they think their team is gonna lose, but IB isn't active right now and is pretty worthless anyways.