Congrats, you'll have a great time so take a breath and relax: You're going to Disney World!
I booked in early May for a late August trip, we got everything we wanted so don't worry you'll have some great meals.
Sharing CS meals: It wasn't a plan per se, but we didn't need more food so we shared. It worked out great for us as we felt like we ate enough and weren't constrained. Personally I think the CS meals are the hidden jewel of the plan - you get enough to eat in the meal; the drink is big enough to share or save for later; the dessert can be saved for a snack or sometimes breakfast (we grabbed yogurt at an evening meal and saved it for breakfast). One tip a CM gave me: order those combo meals ie. side salad, pizza, beverage and dessert. I the salad, nephew ate the pizza and we took the carrot cake back to the room.
I think resort CS beats park CS in most cases. Wide variety in one place, good portion sizes and tasty meals.
TS: We picked places we wanted to try and worked to fit them into our park plans: Boma dinner right after AK closed, Chef Mickey's late breakfast after a late night at Pirate and Princess party; Narcoossee's on arrival night (non park day), Coral Reef we took when we could get the ADR, easy monorail ride over after a long morning in the Magic Kingdom (turned out to be a fantastic break and meal). We chose a Fantasmic package and had our dinner at Hollywood and Vine, that one turned out to be a bit tough to get to as our park plans got a little switched up due to rain, but we kept the ADR and enjoyed Fantasmic and the special access/seating.
Portions: CS meals were plenty generous and easy to share our 3rd was a 5/6yo but we shared 2CS credits each time we had CS meals. We had 3 buffets (Chef Mickey's, Boma and Hollywood & Vine). Given you have a 16yo boy you may want to use buffets strategically as well. The all you care to eat offer an "endless" meal, but never the variety you can get on a buffet. So for hungry, picky eating teens I say buffet. We used Chef Mickey's as a brunch.
Snacks: You may need to police these if your teens have free reign on their cards. A drink, popcorn, Dole Whip, Mickey bar can add up fast! One way to manage this: get some of those things as part of your CS meal(again great choices at the resort) and save for later if needed. You may be able to police the teens or choose another battle. No way to police my mother so I just had to let her enjoy. We would ride, she would walk. We'd meet up she'd have a Dole Whip. Next ride she's got popcorn, then she's thirsty, see the pattern! I'm just glad we had 1 snack credit to give my nephew his itzakadoozie for breakfast on our final morning (hey he's at Disney right? "ice cream" for breakfast once is allowed, esp with his auntie
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Pick some places, make the ADR call and call back as needed it will work out. We even canceled an ADR while we were on our trip: too full to eat a TS meal.
