Stainless Bento Box & Bag for a Tiny Toddler (with room to grow!)

My 14 month old is moving from the infant to toddler room at daycare, and I need to get her a lunch box and insulated lunch bag to hold two snacks and her lunch. I've done a ton of research (including searching posts here), but have some specific questions.

- When did your kiddo start using a full size bento box (like the Rover)? Does it make sense to start with a smaller version, like the Shuttle?

- Has anyone tried both the Planetbox and Good Kiind/Earth & Maker style with the silicone liner?

- Has anyone tried the Fluf Square Lunch Bag? Is it truly insulated and truly washable? And does it fit a Rover?

- Any success/horror stories ordering Amazon dupe bento boxes? I hate buying from Amazon, but the price and free returns are attractive in this case.

Here's my current spec list & frontrunners:

BENTO BOX: stainless steel, as leakproof as possible, dishwasher safe, decent quality and/or warranty, not too cumbersome for a 1 year old
Frontrunner: Aohea (dupe for The Good Kiind)

LUNCH BAG: insulated, easy to wipe out or machine wash, can fit a "full size" bento box (like Planetbox Rover), tough enough to handle a metal bento box
Frontrunners: Fluf Square or Hydroflask