Hi fakeplasticdreams !
No problem with the title, it's quite clear that way

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1) Ahah, good question. The first gen has a flat back, like this :

And the 2 and 3 gen have a curved one :

2 and 3 are working with Everyday Looper, but you will need an external mic. If you have a 3 gen, a headset (so headphone + mic on the cable ) is bundled with it, so you can use it.
If you have a 2 gen, you will have to buy one.
OR
2) Use the PRS GuitarBud cable instead of an headset

. If the GuitarBud works well for you in JamAmp it means that :
- You have at least a 2 gen iPod
- It will work in Everyday Looper
3) It will work on whichever you prefer.
You are welcome

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PS : Does the GuitarBud cable works well for you ? No problem with random unwanted iPod launch during the use of JamAmp ? What kind of guitar do you have ? (That's info for my personal use

)
Raphaël