All of these insulated bags except the Skip Hop one work well with the Easy Lunchboxes: https://www.yummytoddlerfood.com/best-insulated-lunch-bags-for-kids/ Just add an ice pack and you’re good to go.

Depending on which foods you’re packing, you could do one larger lunchbox with everything in it or one lunchbox and two snack containers or a few snack containers. Or two of the Easy Lunchboxes or Lunchbots Trios would be smaller and less bulky than a full size lunch box (and you could use them for years for regular lunches after)

The Bentgo one is pretty easy to open and it is fairly leakproof in our experience so you have a range of options with what to pack. The lunchbots one is super easy to open but it is not leakproof so no wet things like applesauce or fruit cup or yogurt would work in it. I’d practice at home with him, but my 2 year old can unlatch the Bentgo and just needs some help remembering where to put his hands so it stays flat when he opens the rest (that’s hard to explain but I hope it helps!)

Not personally but I have heard good things!