Let's see here. I think where the player first started playing doesn't matter much. I'm the example of someone who has jumped around quite a bit in this series. I went in this order

IX (My Favorite)
X (Liked this one)
VIII (Enjoyed This)
X-2 (Was OK)
IV (Really liked it)
VII (Meh)
XII (Really liked it, but only for the gameplay and not the story)
VI (Disappointed)
Next two are most likely going to be
V
XIII

I'm not sure if I can really speak on it. I have only played eight games out of the series and always had another to play while I was waiting for a new one. I also can't speak on XI, XIII, or XIV either, but going by general opinions I am a bit worried.