The Caro-Kann
Even a relative beginner like myself can probably come up with at least 10 Reasons to Play the Caro-Kann, but I can also think of One Good Reason Not To, at least at my level. By the way, that image is the typical opening few moves of the Caro-Kann, making it instantly recognizable.
I got interested in the system because of my game play with Team Canada Vote Chess, which I highly recommend to anyone active but particularly for relative beginners like myself. You're playing with people from your own country and because of that common bond it is usually really polite and there are no stupid questions.
We have National Masters answering noob questions and giving playing advice on Team Canada. So look around for your major national team and you'll get a lot of regular game play and a lot of good playing advice.
Anyway, back to the Caro-Kann. We played a game as Black, which for me was very instructive. I don't hate playing Black. I just hate playing Black, partly because I don't have much repertoire in my game featuring Black. It turns out the Caro-Kann was just what I needed. It's very well defined with sound theory and it's played at top levels, so even with just the basics it's fairly easy to follow a game in progress.
It's also remarkably flexible which may not be a good thing for a relative beginner. This game line takes practice to recognize what your opponent is doing, particularly if it looks like he or she is going "off the line".
I asked my coach at the time for a book recommendation and he immediately came back with Schandorff (ISBN 978-1-78483-115-8 or Hardcover 978-1-78483-116-5). That was back in early June and I'm not even half way through the book. I play a lot of the variations in the Chess.com classroom to try and see why an opponent might go one way, instead of a more accepted "main line". This book is going to take a while.
I have built myself a couple of cheat sheets of moves from games that looked interesting. We can't use those cheat sheets in game so it's going to take quite a while gain a thorough understanding of the system.
That brings me back to that One Good Reason Not To Play the Caro-Kann. It's really easy to go "off the line" and opponents at my level often don't realize that they're probably way better off sticking to main lines, rather than making up their own stuff.
In his own blog Levy Rozman of Gotham Chess did another of his famous "I Quit" videos featuring a game review of two players, around my level no less, who went and played probably the worst game of Chess ever because they did their own thing.
https://www.youtube.com/watch?v=D7YLHXMhWRo
Hilarious to watch and I want to know why I don't meet opponents like that more often. That would help my progression, and quickly too. Don't get me wrong. I do meet some like that, just not too many, and not quite that absolutely horrible at the game.
