This really helped; hope it'll get integrated into QuickStart for future testers.
Isn't the offline trial activation process meant to generate the license key, in cases where it doesn't automatically do so (even in internet connection)? In this case, it works, since we verified that license is read by RS Connect.
We're in contact with @rachael already; hope to have a conclusion to our evaluation soon.
Thanks again for RStudio team's help.