I think from 6 to 8 is probably fine, but if you're not sure, I'd keep up with a cup a milk if it makes you feel better. We probably stopped my son's bed time milk around that age, but we eat a pretty late dinner, so it's not that big of an issue for us. I would say keep at the table foods too and maybe give him both table food and purees at meal times. 6 teeth is actually pretty good, so don't worry about that, he'll be able to eat the food. He's still within the normal range to eat purees, for boys I think it's more common to stop them between 12-18 months, but keep trying b/c the table food is so much easier!! You can also transition him to milk in a cup too. The longer you wait the harder it will be to get rid of the bottle. Even if he takes a long nap in the afternoon I would still put him to bed at pretty much the same time every night. Getting a routine will help both of you! Good luck!