Well-if you're waking up at 3am you probably aren't eating enough!Seems like your diet is really healthy so if you can't pack in any more you might have to add a little junk to get some extra calories;) or maybe just keep on snacking throughout the day.(trail mix,etc anything calorie dense).
I add avocado to just about everything (or cheese or nuts) when I feel like I need extra because it's easy to eat.Also ice cream-for me an easy way to get extra calories cause I love it(I know I know)
I love peanut butter pretzels for long rides cause they aren't sweet,and you can look at the Feed Zone books for other savory ideas!(also just great ideas for your meals in general).

Oh these are wonderful ideas! Time to go get some ice cream.... I'm getting the PB pretzels for this weekend

High quality cereal before bed time.

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All I Wanted Was A Pepsi, Just One Pepsi

Team Zoot, Team Zoot Mid-Atlantic

Skip the ice cream and pb pretzels. Are you counting your calories? What is your height/weight? Eat rice, corn and nuts/avocado (and even clif bars) which will stave off hunger, but at the end of the day you will be hungry when you expend more calories than consume (and increasingly so when there is a bigger and bigger difference between the two). Consume more if you are in deficit and (not trying to lose weight), but continue to consume more healthy choices.

without knowing anything about your composition, daily nutrition, or training, I'd recommend increasing the amount of healthy fats in your diet.

all day long. *don't short the hi nutrient stuff, either (ex: colorful salads).

nuts, olive oils, avocados, the right kind of butter, etc.
all day long

seems to be working here. just my experience to share with you.

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"Outwork your talent." Kevin McHale

This is just my experience of what's worked well for me during big training blocks.

Breakfast before every morning workout (usually 2x toast honey/PB) - I don't do this until I'm at my target weight
High calorie recovery shake after each workout of the day ~450 calories. - If I'm at target weight I will have this after every workout no matter duration/intensity. If I'm trying to make weight I will skip this after recovery workouts.

I try and replace as much of the exercise burn calories as I can immediately after the workout, then just eat sensibly the rest of the day. If I'm still losing weight too fast I'll have ice cream before bed.

All good ideas.
My training has been 3 swims, 4 bikes, 4 runs (1 of which is a brick), amounting to about 9,000m swimming, 8-9 hour bike, and 3-4 hours running/ week. My body comp is average... I could probably stand to lose a few pounds of fat (who can't?), but if I go into race day at the same body comp/weight, I'll be happy and feel prepared.

I usually eat a lot of salads, rice/quinoa bowls, lean protein (chicken, tuna, tofu, eggs, whey powder, etc.), but I just feel like I'm eating SO MUCH. And lately I haven't had a lot of time to prepare, so it's been a lot of sandwiches, pre-made salads, tuna wraps etc. I have tracked my kcals, but mainly from the standpoint of the proportion of macro-nutrients, as calories counting is very inaccurate.... usually about 50-55% carbs, 20-25% protein, 25% fat. I really don't eat a lot of "junk" outside of the long rides, where I'll rely on the simple carbohydrates. I do treat myself 1-2/week... I have a sweet tooth!

I'll start adding some avocados, nuts, maybe increasing my protein sizes. Any other ideas for good-quality high-calorie meals?

nuts are a pretty good high calorie food. And I just snack all day long. Cashews are pretty calorie dense. I'll do Greek yogurt and add things like chia seeds or some granola for some additional calories. Corn Chex and soy milk (I'm lactose interolerant and gluten sensitive). Tator tots are my go to bad for you high calorie item that I can pack away a bunch

"The Feed Zone" Cookbook by Lim and Thomas should keep you fueled, full, and busy.

if not then Corn Flakes... food of champions.