I'm not sure the playoff format benefits skill teams.
They are playing 6 games a day in the NHL. We do not know if the teams will be evenly spread out like a normal playoffs to give each a day or two of rest in between, or if they may crunch them in back-to-backs or doubleheaders for logistics purposes. If the games are scheduled so as not to leave much time for rest the more grinding physical teams will be at a greater advantage than the fast skating transition skills teams, I think.
They can spread them out, and there should be few back-to-backs. The skeleton schedule was released yesterday, giving 10 days for round robin and best-of-five play-in round, and 14 days for each of the four rounds.
Report: NHL reveals key dates for 2020 playoffs, offseason
I can't find the source, but there was another source that had round-by-round breakdowns. They can easily schedule series A at 12 PM on even days, series B at 8 PM on even days, series C and D on odd days. The 3 round-robin games for each team (6 total for 4 teams) should be easy to schedule with no team having back-to-back: Two days of round robin games, rest, two games, rest, two games, with each pair of games having all 4 teams.
The only back-to-backs would be if a team wins a game 7, and has to face their opponent in game 1 of the next round, to which I say - absolutely perfect. But there's a reasonable chance they could adjust the schedule to avoid that.
With no fans in the arena, and a captive audience on TV who will figure out that NESN/NBCSN are "the" hockey channels, there's a lot of flexibility to change the schedule on the fly, moving teams into the 8 PM slot if the original 8 PM series ends early, or switching teams from odd days to even days to avoid the Game 7 / Game 1 situation I mentioned.
As far as an asterisk on the Cup, to me, the only way an asterisk happens is if COVID knocks an entire team out...in which case the playoffs probably get cancelled anyway. I feel like the NHL is exuding a lot of head-strong optimism, which I understand...I just hope they have a plan in place to put on the brakes if necessary. A hospital in Edmonton just had a "full facility outbreak".