Will an iPad fit in this bag?

Full-size iPad? Probably not. iPad mini, probably yes.

Can you attach this bag to a larger bag using molle?

Not Very well. there is a velcro belt loop on the back , but it is not a typical molle size

What is the length of the shoulder strap fully extended?

Didn't measure it exactly..... But for me this is the only con about this bag.... It is short I ordered a separate universal strap

Thinking of this as a bag to go fly with; will a David Clark headset fit in the main pouch?

I use mine daily and it is a great bag. I do not have that big of a headset but my V-Moda LP-2s fit in the main pocket with the case that they come in.

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Tonto: CCW Mini-Messenger Bag w/MOLLE

Product ID: 4355902

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Description

Often a small bag is all you need, or a bigger volume just won't fit in tight quarters. This is where your Sidekick tonto(tm) shines. And since it's equipped with multiple concealed carry areas, It won't leave you unprotected. Often a small bag is all you need, or a bigger volume just won’t fit in tight quarters. This is where your sidekick Tonto(TM) shines. And since it’s equipped with multiple concealed carry areas, it won’t leave you unprotected.

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