After Oscar had been with us a few months and eating in the library, we screwed up our courage to teach him to eat just like a big boy with his uncles. It took easing him into it (we started at the top of the stairs, then most of the way down), but now he has had his personal spot in the dining room for over a year.
Penwiper, on the other hand ... as his birthday passed, we migrated him to a mix of kitten and adult kibble for him. Knowing his confidence around the others, last night we simply set out four bowls and explained to PW where his was (in the fourth corner of the dining room). He was a little confused by me working on the additional bowls, but he settled down nicely.
Nomming occurred, just like a big boy, and his fellow overlords likewise all accepted the new guy into the feeding fold.
This morning was even smoother. I went downstairs, all four boys followed, and Penwiper took his place as soon as his bowl was down. Life is good.