I completely agree with the OP. Having to regrind everything over and over and over without any respite despite having maxed other characters already will get tiring after a while.
Character limit aside, it also hits if you want to, just for fun, make a different character of somethign you already have.
For me, personally, VT II became more fun once i had maxed all my characters and could choose whatever character i wanted WITHOTU having to think “I should grind Sienna… man, this would be more fun with Saltzpyre who’s already 35…”
I also made at opic about the character progression as a whole and how I think it doesn’t feel good and the lack of shared items and currency also plays a role there.