Samba is trivial to set up with swat. The difficulties are in the bizarre syntax and confusing wording of the configuration file. Of course, if you go into Samba without understanding LAN Manager (the most brain dead NOS of all time, and so something that is easy to understand), then you will get out of it what you took into it.
The only vitally important parameters are security (share, user, domain) and OS level (for NetBIOS browser elections). The actual problems happen with synchronizing users on the domain vs. UNIX. That is simple with smbadduser. If you remember that ALL LAN Manager networking is really peer-to-peer, you've got it licked.
There was a parallel in the days of NT 3.51 Server, which was really the same binary thing as NT 3.51 Workstation. By editing the registry, you could convert WS into Server or even a DC - really, the same thing as security=share vs. security=user vs. security=domain. It's really quite trivial. Oh that was a hateful operating system.
Bring it on, game boy.