>1: Is this possible without infringing the generous license agreement?
YES
>Is it ok to use the same Bittrex API key on both machines at the same time?
YES
>If answer to Q1 = yes, and Q2 = No, how can I achieve Objective 1
The only concern is the load on the Bittrex API.
You may balance it nicely so you don't receive warning messages from Bittrex, or even "punishments" like a week API ban or such.
I'd try to avoid more than 1 or a couple of API calls per second (for all the machines).
This may be tricky as it depends on how you run the processes on your various machines.
If you can, make a script or so (like using AutohotKey) to run smoothly each pair one after the other, and running each Gunbot instance one after the other.
Hoping it's clear - but the idea is not to have all them run at the same time, which would throw 20, 40 or 60 API calls at the same time/second(s), which could end up bad.
>1: Derive happiness from helping out fellow members of the gunbot community.
I'm happy
>2: Have a sense of humour.
You must have some in order to make Gunbot work the way you wish it works...
>3: Never have worn a polo shirt with the collar popped (exception for female tomboys)
I don't even know what it is.
Right now I'm naked and wear only wooden shoes