Default Purchase Consideration: iPad (just the iPad)

When to Buy the iPad Air: you want some of the extra features but don't want to take a price jump clear up to the iPad Pro.

When to Buy the iPad Pro: this is the most versatile of all of the iPad products. You get the most powerful iPad chip, arguably the best screen on any apple device, FaceID, and more.

Other Considerations

• Which accessories will be critical for your workflow: keyboards and Apple Pencil in particular are different between models.

• Storage: the Pro models start at 256gb and the others at 128gb. The key here is how much storage space you want for the device. If the devices are going on road trips where you will be without wifi and you want plenty of room for video storage, you should consider going up to at least 256. If you are upgrading from another ipad, go to settings/general/ipad storage and see how much you are using and what is taking up that space. If you are approaching 100 you should consider going up to 256. If you are at 200+, you should consider going up to 512.

Check out apple's iPad comparison page here.