J.X.
As far as the food thing goes, it sounds like he may need more calories, not just larger quanties of food. Jars of baby food are mostly water and don't have the same calories per ounce as table food. I'd recommend trying richer foods like meat, cheese, and yogurt. Even if he doesn't have teeth he should be able to eat ground beef, small tender peices of chicken, or sausage. When my son went through this I took him off baby food altogether and used a food mill to grind up things for him. He loved chicken, rice, green beans, and yogurt all ground up together with some herbs.
My best tip for making all meat easier for the toothless is to use a knife and cutting board to mince it up, and then mix it with a little yogurt if it's too dry. Feel free to email me if you want other food ideas.
My recommendation for the sleep thing would be to do the Ferber method. You let him cry for 5 minutes then check on him but don't pick him up. Next time you check is 10 min later, then 15, etc. You have to be very consistant so he learns what to expect. The first night is the worst, but by 3 nights he'll probably go to sleep pretty easily. My son is very active and has a hard time settling down, but this worked at night time. Now that he's 13 months he can put himself down at naps after some stories.