What led you start playing Hearts of Iron? I never win while playing one game and saw the advertisement of HI and liked it very much.
I'd been playing in a tournament for the FPS battlefield 1942 mod Forgotten Hope. After several campaigns as a grunt I was given a officer position which heightened my interest in WW2 at the strategic level. HoI2 was the first game I found of that genre and I quite enjoyed it. It also let me realize my little dream of a competent Italy taking control of the Med and Black sea.