How realistic is this timeline and how does it look?

I think that looks good! You don't want speeches to be too long anyway!

Maybe you could each ask your MOH and best man individually if they wanted to give a speech or not? You could also ask them to give a speech at the rehearsal dinner instead of the reception!

I personally like MOH/BM speeches because they are normally the people that know the couple best, and spend the most time with them. I will say the best time for speeches and dances I've found is if they are in between courses. That way some people are just finishing up, servers will be cleaning and bringing the next course. Guests can be 100% focused on the speeches and won't distract them from food. Also that way everyone that has a speech will also have the opportunity to eat each course and won't potentially miss one. Especially for you and the groom! It'll be hard enough to get food in, it'll help to have people seated and not coming up to talk to you while you are trying to eat quickly before talking to people in between courses. The paid entertainment I think would be fine to do during dessert, cause then it'll be party time right after!