I'm still fiddling with the variations, but 14.f5 looks like it leads to some interesting play.
Win, Lose, Or Draw? One Take At the Caro-Kann
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I think I like white's position better than black's after 44...Kc7 45.Bc5 Bd6. If the bishops are immediately exchanged, then yes: it looks like it's probably a draw.
But white doesn't have to trade bishops. Instead he could try 46.h4. The bishop trade doesn't look very pleasant for black if he initiates it, since it creates three central connected passers. Thus 46.h4 Bxc5 47.bxc5 Kd8 48.Kf3 b4 49.Kg4, and black's knight would be looking a bit tied up to me, while white's king would be positioned to give support to both his central and his g/h pawns ...
After 46.h4 Black could try instead to penetrate white's position with an eventual Nh5, but if that is played immediately then there follows 47.a3, and black's pawns are pretty much fixed and widely separated. Black should probably try to hold on to his bishop, I suppose.
It's not at all clear to me, except that it's a very interesting game 
frodonbab
Hi. Thanks for the comments and analysis. I agree that Black would not want to take the initiative to exchange Bishops as he would have a difficult time stopping 3 connected-center-pawns with a Knight.
Rather than try to exchange, that's why Black plays 45. ... Bd6 in order to activate his Bishop and prompt White to exchange. If White rejects the idea with 46. h4 then I would force the issue with 46. ... b3! so that if White wants to retreat his Bishop then he drops his b-pawn with 47. ... Bxb4 and one less pawn to deal with!
Overall, I really do think it's the power of the Knight to move fluidly around the board and dominate the light squares that makes Black's defense so resilient. However, I could be wrong. My endgame isn't what it should be =/
Very good point! I didn't see that at all. But white can still hold onto his bishop by retreating it to d4, after 4...b3!, since Black's knight on g7 is hanging. Black defends the knight somehow and then white still gets to play a3, I think. Absolutely true though that the knight is very powerful and hard to predict in this kind of game. I'ld really like to see it played out
Here's some possible continuations had white played 14.f5:
14.f5 gxf5 15.exf6 Nxf6?? 16.Bxh6
15...Kxf6 16.Qe5+ Kf7 17.Qxf5+ Ke8 18.Qh5+
15...exf6 16.Bxf5 Ng7
Bulla
The more I look at things, I just don't like my Queen on the Queenside. But 14. f5 does lead to interesting play because I recognized in the middle game that I didn't want to keep the tension on f6-e5 and I just wanted to Stonewall in order buy some time to develop my pieces. A quick f5 would have prevented me from doing that.
But I would probably answer 14. f5 with something like 14. ... Nf8.
For the past week or so, I've been toying with the idea of adding the Caro-Kann Defense to my tournament repertoire as a alternative defense to 1. e4. This is an OTB game played at a local chess club where I was thrust into the role of acting club director. Right before we played this game, my friend tested for a performance rating of approximately 2000 USCF, so I knew I was in for a fight.
White enters the middle game with what I'm guessing is about a +/- advantage and maintains the initiative throughout most of the game, but Black has a overall solid position that is difficult to crack (if you don't mind playing defense). White made an interesting sacrifice with 30. Bxf5!? exf5 31. Qxd4+! opening up the position and gaining 3 pawns in exchange for a piece. And during the game, I felt White missed an opportunity to win a pawn with 38. Rxe7? where 38. Rb6! would have been better.
Someone was waiting in line to play me, and the game was down to the last few minutes, (and I play a somewhat weak endgame), so I blundered with 44. Ne8?? 45. Bc5+! Down one. But the endgame position was interesting with 3 pawns vs. piece. During the postmortem, we picked up the game from where we left off, and with more accurate play, we both felt this game should end up drawn. White has strong central control, threatening to Queen, but Black's extra piece is very powerful, capable of punishing White for his total lack of light-square control.
From the following position, what is the result of this endgame: win, loss, or draw? And as always, any middle game tactics you spot are always welcome: