D.T.
My daughter ate when I ate. Three times a day, then directly after she got her cup of milk/formula. For me a tall bottle fit into a handled sippy cup. I found out by mixing up a bottle and then pouring the formula into a cup. She would sip at it all day and once it was empty I would just fill it up again. Breakfast after she woke up (baby cereal, and fruit). Lunch around noon after first nap (veggies, bits of what I ate and fruit). Dinner around 6 after second nap (veggies, bit of my dinner and fruit). You can always start with half the veggies and half the fruit from the cups, he's old enough to push your hands away and squirm away from you once he's done. That's how I did it.
Good luck.