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Q: Will this hold a Novolog and Levimir pen together?

It will hold a novalog & basalgar don’t use Levimir if about the same size don’t see a problem

Q: Can I order extra inserts?

We have not sold on Amazon inserts. What's the problem with you? You can contact me through the mailbox. I'll try to help you solve it

Q: Does this case have enough room for 5-6 vials?

Two or three Stelara injectors fit. I don’t know about insulin vials.

Q: How long do I chill the ice packs before using in the case

I chilled them for a few days. However, it didn't stay cold. Next time I am going to put an additional pack in there and put the pen between the packs or use other packs. I would test it before you travel to see how long the packs last, and maybe use different ones than the ones that come with it.