I'd imagine that ARMS will get a sequel on the next Nintendo system. If Sakurai (or whoever is directing the next Smash game) is made aware of the sequel, he'll likely take ARMS into consideration for the next Smash game. Though as was the case with Splatoon in Smash Ultimate, they'd mostly pull from the first ARMS game in Smash 6/7 in this scenario.I'm not taking Spring Man as a next Smash lock because it's so far out we won't even know the state of Nintendo 1st party by then.
Olimar isn't as good a comparison because Brawl's project plan was made in 2005 which was 1 year after the release of Pikmin 2. If ARMS 2 manages to get released somewhere around 2021 to 2023 then I think Spring Man has a great chance. Else I don't think Sakurai would be revisiting 2017 games for what would be like a 2025 Smash game. (Heck the next Pokemon rep may be from Gen 10 at that point. lol)
As for Pokémon, it could end up being the Gen 9 rep if there's a 4-year gap between generations going forward. If it's 3 years between each new generation, then yeah, it'll probably be Gen 10.