You're pretty much stuck when it comes to looting and talking to NPCs I'm afraid.

I don't know anything about Octopus, so I'll defer to others for specifics, and as a Keyclone user I haven't had to worry about the standalone maximiser so I'll duck out of that one and defer to more knowledgable people there too

In terms of nice tips and experiences, these forums are absolutely crammed with them. I'm quite sure I would have given up months ago had I not been motivated by the achievements of others.

To answer your Octopus (which is free) vs. Keyclone (which will cost you $20 per PC) question, in your situation I would have no hestitation in recommending Keyclone. The author has made a name for himself not just by having a good product, but by personally guiding people through exactly the sort of setup you're talking about here.

I've no doubt that he would happily dive into a voice chat with you, and during that he'll certainly solve your maximiser problems.

As a first-time boxer, I would start simple. Try boxing classes that synergise well ('n' casters, for example, even if tha casters are different classes), and only start going into Holy Grail territory when you're comfortable with the basics.

Once you get past the technical challenges, there's no substitute for just "doing" boxing and seeing how things interact. You'll be amazed how fast you learn once you get to that stage.