Noted on sketching on the ipad & uploading - good one for the feature hopper (cc @Tony).
@nateva, few threads here on starter CAD, but anything that can output as DXF or SVG should be fine - but we use Fusion360, Rhino, and Sketchup in the office often FWIW. (I’m probably forgetting one).
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I have Paper 53 also. It’s beautiful. I am planning on buying a new iPad in Feb. My old iPad is an original. I’m hoping to better serve myself and my Glowforge with a new one.
Maybe I’ll start them with sketching then move on to some type of CAD - the good thing about the wait is that I have time, the bad is, obviously, that I have to wait!
Thanks for the suggestions
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As a software developer reading this thread the first thing that comes to mind is creating an API and then letting the open source community at it to create plugins for apps they want to interface with Glowforge.
Granted, official plugins supported by the manufacture are nice also 
One of the primary reasons the Glowforge caught my eye was the ease of use with Illustrator. I’d definitely want to give the plug-in a try beforehand to plan out some design strategies and see what can/can’t be done quickly.
You should speak to GravitySketch, they have a beta 3D sketching program, could be useful and they could output a format compatible with Glowforge