we had a problem with my DH's lunch and no don't use a bento style - so I don't know if this will help you or not
we got a good deal on a 6 pack size zip insulated bag - I got 3 for 99 cents each at the end of the season as CVS and have had them prior- they last for years
we have been using small glass container (Libby glass) and safe plastic lids - I got them off a green natural site and we also use brown wax bags - the bags are great for items and can be used several times and get composted
due to what my DH takes - mostly cold beans, yogurt, oatmeal they fit great in the bag a long with a mug and I got lots of bandana (napkins)- throw in a fruit/veggie and the stuff doesn't bang around
his is the only lunch I pack - we just found it to be easier to clean and store a head of time in the frig vs a large container I don't have space for when I get lunch ready the night prior
the small glass works really great for us, right size, easy to stack and clean - I had gotten 8 of them - this works really well for making oatmeal on a Monday and I can put it away and fill the next day - and for him on Mon I add instant oatmeal and dried fruit in the glass and he just needs to add hot water, it's great for yogurt, we use a large size, I add fruit (frozen) and plain on top - cuts down on cost
this is what works for us because he leaves at 5AM, he just takes out usually 3 container and a bag and pops them into his bag
Dh is the only one I pack a lunch for. We got the Laptop Lunches box, insulated bag and an extra set of inner containers for him a few years ago. It has all held up very well even with being washed and used 5 days per week. A bento kit costs about $38.
I like that the containers are not fixed and can be put in several ways to fit different sized foods. I use it without the containers sometimes too. It holds plenty of food for my dh.
We've tried lunch boxes but DH, DS and DD (both teens) find they don't really work well for their needs. Typically, the portions are too small. Also, they are often taking leftovers. A separate thermos or glass container with a tight fitting lid works better than a large fixed container with lots of little spaces. They have used retro style school lunch boxes and some Tupperware lunchboxes we came into that have separate compartments, but for a few years now these lunch boxes have been unused and cluttering up my kitchen cupboards. Instead, we use assorted sizes of glass Lock'n'Lock containers, thermoses, mason jars and a few smaller containers. They also find that a large, rigid container is awkward and often doesn't fit well in their bags. With smaller, separate containers, they can slip them into different spots in their backpacks. I know you said you want 3 identical bento-style containers but you could buy multiples of single containers and keep them collected together in a larger lunch box or lunch bag. Just a thought.
Yes, that is a big drawback with glass. We just lost a bunch in a kitchen accident. Our dog's collar caught on the drawer handle and he pulled the entire drawer onto the floor. That was a pain to clean up. It's making me reconsider glass, although it was a fairly unusual event.
I also like the look of stainless steel tiffin containers. I'm considering getting a few as replacements for the glass containers we just lost.