[notahacker]

In repeat games your friend's strategy might actually be counterproductive, assuming he's playing against people that are rational enough to figure out that he always starts offering a draw round about the time he expects to lose, but not so good at chess that they sometimes don't sometimes miss opportunities for a quick checkmate...

I'd be disappointed if an AI chess computer invariably let me know that I had a better path to winning the game than it did.

[gkilmain]

That is exactly what happened. He played a friend of mine whose much lower rated. Eventually the lower rated player found himself in winning position but when the draw was offered he assumed he must be missing something and accepted it. So it worked once.