I can relate to a lot of this. Sometimes what is supposed to be fun feels like effort. This is the main reason I'm looking into building a pit - something I can just hop in and go. I also seem to start on new titles very late and it just seems like I'm way behind everyone else. I'm hoping that A-10 will be the first time that I get in when the door opens and learn as everyone else does. It's hard jumping in even a year later and having to go through mounds of information to get up to speed.
