Welcome back. So not sure I could speak on the difficult level. Set up is pretty simple. There are videos that walk you through getting a small team together and into battle (see Sic's post above). I think the tools here will give you the closest experience to a live group. The main objective is have a full functioning group with minor input (within the games TOS limits of course).
Kissassist is a very powerful tool so I would say focus on learning that first, and then later if you want to look into the plugins or other apps trying them out and see what fits best. But that all starts with the setup videos.
Word of advice: It is so easy starting off to go down a rabbit hole and forget what you were initial researching. If you find items that you might want to research later, bookmark it. At the top of every post there is a little icon on the far right for bookmarking. Click it, give is a good name and description, and save it. You can return to your bookmarks by clicking on your account name on the very top of the page, inside that there are 2 tabs,
Your account | Bookmarks. It will come in handy when you want to load up some of your favorite resource ini files.
Sorry I know you were looking more for a difficulty rating but I think if you have gotten this far its better to just dive in and see for yourself.
