While I can feel your pain JonP (and yes, i have more than once pulled out some of my remaining hair when frustrated with the way I "thought" Aware configuration should work), I have to assume that your "expert" perhaps has a different skill set than is required.
Yes, there are some config files that have to be edited (but they are well documented in the installation guide) and while it would be great to have a GUI for all of the configuration changes, This should not be that difficult.
Every remote server setup (whether you say Cloud, or AWS, or RackSpace or ....) has different ways to configure access and port forwarding. This is where your network "expert" might be of more assistance. Whether you use RDP, or a VPN, or .... once you are not on a LAN, then you might have some "fun" connectivity issues.
Btw, Mark, since so many other programs use either port 80 or 8080, I always change my Aware Port to something that I expect no one else to "hog". That seems to be easier than tracking down what other app is using one of these common ports.
While a GUI is the norm in the windows world, so many servers are LINUX based since a lot cheaper for similar horsepower (ok, forget the fact, perhaps less likely to be hacked... etc.), and there, a GUI is not the norm. Good news, once it is set up, its easy peasy to launch with a shell script but if you dont know how to start / kill processes, then you need to have access to someone with those skill sets.
I know aware's marketing says "no need to know SQL, etc. etc." to build robust applications, but I think that selts false expectations. If you don't have a knowledge of SQL, CSS, database design, and of course, the ability to not just set up your server, but to maintain it. you are severely handicapped.
Even if Aware had simple, automated installation for a server (or, in your case, the cloud), without knowing how to check or memory leakage, killing and restarting processes, you are sort of driving without a seatbelt (or airbag and not the exploding airbags)
But, this is just MY opinion, I might be wrong...
Bruce