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When trying to gain weight (or simply not go minus as in your case) the method will be the opposite of what is needed to lose weight. I have helped someone with this in the past and what I saw as his greatest trouble was that he would get too full to eat more very quickly. I asked about his diet and it was just full of foods which are very filling without actually containing many calories. Lots of fruits and vegetables with almost no carb and no fat.
So really what you need are easily digestible and not too filling calorie rich ingredients. Think lots of grains and fat. Buttered potatoes instead of air fried potatoes. Carrots instead of lettuce. White pasta over whole grain pasta. Cream or mayo based sauce instead of a stock/water based sauce etc. However still try to eat healthy. If going for bread take the white bread without added sugar for example. And still include vegetables but don't make them over ⅓ of your plate. I have read many success stories with adding heavy amounts of dairy to the diet which makes sense since milk is there to grow a calf as fast as possible. Drinking a package of milk a day is almost a miracle cure to being underweight if you can stomach it. In fact the medical food packs they give to malnourished children are dairy based. Consider it if your diet allows it.
However what specific meals which are convenient to bring I don't have many ideas. But I hope this mode of thinking will help at least a bit. It has to be a big portion that you can actually stomach. Think about which foods you seem to be able to eat a huge amount of and then narrow those down to the most calorie rich. They also have to not clog your stomach for the whole rest of the day so being easy to digest is also key.
I'm basically in the same boat as OP except opposite job direction (went from labor to desk). Over a decade of manual labor with no scheduled lunch breaks has left me with poor eating habits. I tried meal prepping but ended up doing what your friend was doing, loading up on fruits and vegetables with some protein. Wouldn't eating stuff like buttered potatoes and drinking a couple glasses of milk everyday lead to heart problems? Or would cardio and being underweight basically cancel that out?
Fat has been way over demonized in modern times, it's nowhere near as bad as people think it is. There are some unhealthy trans fats, but those have been banned pretty much everywhere.
My brother in Christ, I'm GenX. We were brainwashed to hate fat. And I've never been a fan of fat on my meat, not even a little. It's been a time trying to get over that aversion.
And of course they were pumping us full of straight sugar. No problem with that!
Now I eat bacon and butter all day long. And guess what? I have energy when I do that and it tastes better. (I know, I know, moderation in all things.)
There's things to be concerned about still, but it's mostly about the ease of consuming a shit ton of calories with oils. Using real butter or eating fattier meat isn't really a problem.