I can understand your frustration. However, we never plan our
Disney vacations 180 days out or more - and sometimes it's less than 60 days and we have always gotten to do everything we wanted (even with a large group of 8 last summer).
I have been able to book hard-to-get ADRs with less than 60 days to go. It takes some stalking and extra time at the computer. Others have had success using a reservation finder. I would suggest that if there is any place you think you might want to eat that is difficult - just book the ADRs now and cancel or modify them later if your friend decides closer to the trip to ditch the meal.
I have traveled with others to Disney multiple times. I think the most important thing to keep in mind is that not everyone 'does' Disney the same way. You don't always have to be together. I'm sorry - I'm not going to go on Splash Mountain - I hate being wet in the parks. But, I will be more than happy to hang out while everyone else goes on. I love Peter Pan and would use a fastpass on it every time I visit MK - others, not so much. So, I get my fastpass for it and they get one at the same time for something else. I don't like SciFi, but my sister's family loves it. I got them and one of my daughters an ADR for it and took the opportunity to hang out by the pool while they ate and my husband and other daughter were visiting Harry Potter. Divide and Conquer.
Also, I didn't read all of the responses, so I hope I'm not repeating something. In terms of your friend not liking buffets, but wanting a character meal. Trattoria al Forno has a character breakfast that is plated individually other than a shared bowl of pastries. It's easy for everyone at the table to pick up a pastry without touching the others.