Foods that are healthy and have many calories.

Good oils - olive or canola, for example. Nuts, seeds, peanut butter and other nut butters. Beans and whole grains.

Do you keep snacks around (boxes of crackers, chips, other snacks)?

I find, feeding a young family, that those types of snacks prevent my little ones from having an appetite for the real meal I fix, including the veggies. So I don't buy fruit juices (our beverage is water), or snacks. Our snacks are like mini-meals, or maybe fruit. I usually have meats roasted and ready to go for any use, which makes putting meals together 100% easier!

Also, do you have a meal that you sit down and eat together?

It's often lots of clumsiness and noise, but my husband reads a story during dinner, or we talk about things. We do a lot of correcting of table manners lol, but this is a time to eat and not solve family probs or air grievances. So the children I think learn to eat better from doing this.
So like tonight I reheated some roasted chicken and herb/cheese potato fries. Each person snapped off a whole romaine leaf, drizzled some dressing on the leaf, dusted it with a little parmesan, then used it to stuff their dinner in it while they ate. The children thought it was fun!

coconut oil, butter, cashew butter

I don't have any children. But growing up, you either ate what was cooked, or you didn't eat anything.

Maybe your boys need a little "tough love" for the sake of their nutrition.

His nutrition is fine. Perfect health for a kid his age.
But just as my mother did to her 4 kids, and my grandmother did to her 11- no kid goes to bed hungry.

But this is more about what I can make as a family that will still help me out at the same time- not forcing everyone to follow what I eat. That's just rude. Lol

How can someone's nutrition be "fine" without vegetables? And you're not "forcing" him if you're his parents. You're just doing your job.

Do you keep snacks around (boxes of crackers, chips, other snacks)?

I find, feeding a young family, that those types of snacks prevent my little ones from having an appetite for the real meal I fix, including the veggies. So I don't buy fruit juices (our beverage is water), or snacks. Our snacks are like mini-meals, or maybe fruit. I usually have meats roasted and ready to go for any use, which makes putting meals together 100% easier!

Also, do you have a meal that you sit down and eat together?

It's often lots of clumsiness and noise, but my husband reads a story during dinner, or we talk about things. We do a lot of correcting of table manners lol, but this is a time to eat and not solve family probs or air grievances. So the children I think learn to eat better from doing this.
So like tonight I reheated some roasted chicken and herb/cheese potato fries. Each person snapped off a whole romaine leaf, drizzled some dressing on the leaf, dusted it with a little parmesan, then used it to stuff their dinner in it while they ate. The children thought it was fun!

Most snacks are the fruits. Bananas, yogurt, saltine crackers, and peanut butter on a spoon are the usual. I don't do snacks, though, because I only eat when hungry. The idea of eating when not hungry is just strange to me. My husband boredom eats, and that turns me away from eating when not hungry even more.

My son and I eat breakfast and lunch together. All 3 of us have dinner together. (My husband works midnights, so he sleeps through breakfast and lunch.) My son helps me cook, and we have everything on the table when eating. I'm not much of a person who believes in eating in front of a tv or on the couch. I love the family time. It's just us three, so there isn't much noise. Our little guy just eats and then gets up to go back to playing while my husband and I converse afterwards.

The most 'creative' stuff we do is with home made pizza or experiment with flour/dough mix with home made cookies. I don't usually eat either since my son is the one with the ingredients. Lol

It's really great that you have that awesome habit...eating when hungry instead of when bored/etc!! I'm sure your son is learning from your example! Definitely, making meals for a family is an art form! For me, having meats already roasted and ready (either in the fridge or freezer) is a must, because they can be used in so many different ways, and for any meal including breakfast! I also usually make a big salad that stores well for a few days...it ends up getting eaten for all three meals, even by my children...I think because they watch us do it, and ends up sounding good to them. I have cottage cheese and yogurt on hand. Canned tuna makes a quick tuna melt, or a dip with veggies and crackers. Hors d'oeuvres can make a fun fun meal and you can really get creative out-of-the box with these--totally fun!

Most snacks are the fruits. Bananas, yogurt, saltine crackers, and peanut butter on a spoon are the usual. I don't do snacks, though, because I only eat when hungry. The idea of eating when not hungry is just strange to me. My husband boredom eats, and that turns me away from eating when not hungry even more.

My son and I eat breakfast and lunch together. All 3 of us have dinner together. (My husband works midnights, so he sleeps through breakfast and lunch.) My son helps me cook, and we have everything on the table when eating. I'm not much of a person who believes in eating in front of a tv or on the couch. I love the family time. It's just us three, so there isn't much noise. Our little guy just eats and then gets up to go back to playing while my husband and I converse afterwards.

The most 'creative' stuff we do is with home made pizza or experiment with flour/dough mix with home made cookies. I don't usually eat either since my son is the one with the ingredients. Lol

It's really great that you have that awesome habit...eating when hungry instead of when bored/etc!! I'm sure your son is learning from your example! Definitely, making meals for a family is an art form! For me, having meats already roasted and ready (either in the fridge or freezer) is a must, because they can be used in so many different ways, and for any meal including breakfast! I also usually make a big salad that stores well for a few days...it ends up getting eaten for all three meals, even by my children...I think because they watch us do it, and ends up sounding good to them. I have cottage cheese and yogurt on hand. Canned tuna makes a quick tuna melt, or a dip with veggies and crackers. Hors d'oeuvres can make a fun fun meal and you can really get creative out-of-the box with these--totally fun!

I eat celery instead of salads for that reason. I'm the only one who eats salads in this house, so it goes out too quickly and I have to trash it. But ants on a log? That NEVER gets old.
Cottage cheese.. yet. We get the 4% kind since it's not too bitter. That and some goldfish crackers are the best.
I will admit I've been eating a bit less than normal lately, but it's because I'm getting off birth control after 5 years. Body is in for a big change and I'm here and there.

I avoid freezing meat, but maybe I should start. Chicken and Deer will stay juicy even when frozen, right? (So new to the freezing!)

Juiciness will not be an issue.
You can roast a chicken in the oven (just put into a very deep pot, uncovered) No need to add anything, just roast it until it's falling apart, and deep golden brown. Then freeze the de-boned chicken in a ziploc, flat so it's easy to break some off for use. Alternatively, your hubbs may enjoy BBQing a couple whole chickens for you, beer can style. Or buy a couple rotisserie chickens, that's better than heating up the oven in the summer. I don't like to roast a chicken in the house, but since I have a whole house fan to remove the odor, I'll do it.
Ask the meat-person for a 4 lb cross-rib roast...it's a good price and excellent flavor! Have the meat-person cut it into slabs for you so you don't have to do all the cutting after it's cooked. Place the meat into a big lasagne dish pan and slather with unrefined salt, garlic powder and black pepper...use plenty of seasoning. Cover the dish tightly with a generous amount of aluminum foil so the moisture stays in the pan. Bake at 350 degrees for about 3-3.5 hours (until the juices are becoming dark brown). It smells awesome and the flavor is amazing! Check at 3 hours, roast longer if needed. Freeze some in zips, but this meat will taste awesome for days in your fridge!

Do you happen to live near an Aldi grocery store? Their prices for produce are much cheaper than other grocery stores and much of their other merchandise is generic but of good quality. If there's one near you it'd definitely be worth your while to check it out for chicken, other meats, peanut butter, avocado, breads, eggs, milk, etc.

I'm not sure I understand the original question? You are looking for healthy, calorie dense foods, which are inexpensive and also suitable for your son? Is that right? Are you just tying to get your cals up to your daily goal? How far short are you falling?

Juiciness will not be an issue.
You can roast a chicken in the oven (just put into a very deep pot, uncovered) No need to add anything, just roast it until it's falling apart, and deep golden brown. Then freeze the de-boned chicken in a ziploc, flat so it's easy to break some off for use. Alternatively, your hubbs may enjoy BBQing a couple whole chickens for you, beer can style. Or buy a couple rotisserie chickens, that's better than heating up the oven in the summer. I don't like to roast a chicken in the house, but since I have a whole house fan to remove the odor, I'll do it.
Ask the meat-person for a 4 lb cross-rib roast...it's a good price and excellent flavor! Have the meat-person cut it into slabs for you so you don't have to do all the cutting after it's cooked. Place the meat into a big lasagne dish pan and slather with unrefined salt, garlic powder and black pepper...use plenty of seasoning. Cover the dish tightly with a generous amount of aluminum foil so the moisture stays in the pan. Bake at 350 degrees for about 3-3.5 hours (until the juices are becoming dark brown). It smells awesome and the flavor is amazing! Check at 3 hours, roast longer if needed. Freeze some in zips, but this meat will taste awesome for days in your fridge!

That's good, then. I usually put the chicken in the crock pot and then the oven just wrapped in foil with the corn. We never buy boned chicken. Just breasts. I dont do ribs either.. I pick at any fatty like piece.. Those my boys ADORE ribs.
(I'll also be looking up what beer can style chicken is.. Never heard that term.)

I'll get this copied, though. I mainly cook chicken breast, brisket, lamb, deer, and buffalo.. but I love new things regarding meat. Thanks!

I've not tried those meats, and I should:) If you ever do a whole chicken, you can use the bones to make broth...just put the bones/cartilage in a roomy pot with some basic veggies like carrot, celery, onion, parsley, add water until covered. Bring to boil then lower heat. Let it simmer, barely bubbling (harder simmers will emulsify fats and make a cloudy broth), until the veggies look spent. Strain and freeze! It's delicious if youdrink it like broth in a mug, with a squeeze of lemon and some additional seasoning, or make a soup.

cheese. (add it to broccoli, if you're interested in adding veggies.)

salad dressing, like ranch, for dipping (carrots, celery, chicken, pizza bread.) it sounds gross to me but my kids would eat things dipped in ranch that they wouldn't eat otherwise. the salad dressing isn't "healthy" like you requested, but the dippers can be.

and again, nuts. i could eat peanut butter all day long but i'm trying to keep my calories down.

oh, and my kids LOVE spaghetti. marinara sauce and sausage/meatballs on the side.