I started with Trails in the Sky, gone through all of the first and most of the second. Despite the total look of the game I gave it a shot. For whatever unexplained reason I'll get hooked on it for hours at a time. I'll probably start Cold Steel series later this year, they are much more modern in presentation. There's something about Falcom games that I've gotten in to in that they are like comfort food for me, they aren't necessarily lookers but I always have fun.

If you end up liking Trails, you might try one of the newer Ys games, very under-appreciated series. I never know with a From Software fan though, they are much more button spam hack and slash than the slower Souls combat.