So this is an interesting questions and I want to see if @dan can chime in but I’ll take a shot at it because of my understanding from reading the forums.
From my understanding the GF will have a cache that will hold recent jobs, this means that the design doesn’t have to be re-downloaded from the cloud BUT the GF is controlled from the web essentially. This means to run anything you would have to be able to communicate with the GF regardless if the design is in the cache or new. I also don’t think it works like a standard printer and that it can just spit out copies. It has to scan whats in the bed, you have to align the design then it will cut. If it were to do that you would have to put the material in the exact same place every time. That being said you could have 10 individual pieces of material and cut 10 luggage tags in one job.
With the second part
if the wifi was lost the job would finish if it was in the cache, if it wasn’t then it would pause and then resume when the connection was re-established.
I also have a suggestion for your wifi issue. – You could set up your own little network just for your Glowforge. Something like an Apple airport express which can take and ethernet connection and create a wifi network, this would be perfect (and its cheap, you could pick one up on eBay for little to nothing). Then your Glowforge sits separate from everything else. I don’t think you would have to even be on the same network because it runs through the cloud (like the demo video they just released click here)