Best Starters: Any FF made after FFV. Starting with VI the series has incorporated more user friendly elements to make the games easy and enjoyable for newcomers.

Worst Starters: Any FF made before FFVI. There's a reason their called Old-School FF. If the guy doesn't walk away from being bored by the lack of constant gripping story and character drama, he'll certainly leave in frustration by the entries difficult and archaic game design.

Jordan: DAMMIT! I hate this game! I just several hours of work cause I got hijacked by a some powerful monsters and I blew through all of my items and MP. This game is just obviously terribly designed.

Me: Why didn't you save more often so this wouldn't be such a loss?

Jordan: Um, because I only need to save when I'm done playing, tard.

Me, Um, no dumbass. You should be saving anytime you accomplish something noteworthy, even if it's just a level up. These games can be brutal and you never know when a battle may go south for you. You know "save often".

Jordan: Whatever, this game is just poorly made...

Me: I knew I should have just drugged you and harvested your organs for the black market instead...

Jordan: What did you say?

Me: I said you might have better luck with these two other series I know: Shin Megami Tensei and Dark Souls. How about I get you a drink wile you settle in and familiarize yourself with the games?