>>55913713Brock abandoned his medical career for a girl
who already had a boyfriend.The most successful main characters so far would be:
Gladio/Lillie inheriting a multi-million dollar foundation, this position is more due to nepotism, although Gladio could easily become a captain or Kahuna. Similarly is the case with Bianca, we will never know if she became a researcher like her BW2 counterpart, so she probably lives off daddy's money.
Ash being the reigning world champion could be backed by a lot of sponsors and brands as was the case with Leon. Similar for Iris but in a more local way, being the Unova champion, these are the equivalent of super athletes and political figures in our world (Imagine Putin winning Olympic gold by kicking a 10 yo kid)
Marina, being a successful Idol in at least three regions (Johto, Hoenn, Sinnoh) in-universe, has been sponsored by different companies, has a fan club and has the title of Top Cordinator, something that none of the other girls has achieved.
Gary as a researcher, both through the support of his family name and on his own, it has never been shown how much researchers in that world earn, but most seem to be well funded, in addition to the fact that the Oak family has strong influences.
Regarding the others, their closure was not so bad, many have a position as Gym Leaders or candidates like the case of Paul, the rest of the Alola gang chose something more mundane unlike their video game counterparts, highlighting Sophocles wanting be a space engineer, which is not bad at all.
If I had to choose who had the most meh ending, it would be Cassie, she never achieved anything in her league and I think her biggest dream was just supporting her favorite team, not even wanting to be part of the team, just supporting them from the stands.