Ok so I'll admit it, when I was growing up I wasn't much into Rpgs, so  I actually missed a lot of the great ones on the SNES, Genesis, PS one, heck even the PS2. But now that I really love Rpgs I'm trying to play all the good ones I missed. A particular series that I'm dying to play is the Tales of Series, especially to prepare myself for the Tales of Vesperia PS3 english release which I hope comes out this year.

Long story short, here's a couple questions.

Does it matter in what order I play them?

Which do you recommend I play, which ones should I skip?

Should I even bother with this series?

Also, which one is your personal fave?

Good choice.
None of them are directly related unless they say so in the title.

Play:
Phantasia (GBA,PSP)
the Abyss (PS2)
Symphonia (NGC)
Vesperia (360)

SKIP:
Symphonia: Dawn of the New World (WII)
Lagendia (PS2)

I havn't played the PS1 games, so I can't offer any opinion on them. Hope this helps.

Abyss is my personal favourite and those are some good recommendations (I'd also throw Tales of Destiny into the mix, if you don't mind replaying older stuff). Regarding Phantasia, I love that one too, but the GBA version is an almost completely botched port+localization and the PSP version is only in Japanese. There are however fan translation patches for both the original SNES, as well as for the PS1 remake versions (otherwise not released in the West)... I'd recommend those.

P.S. There is a Tales of Destiny and a Tales of Destiny II in the US, with the latter actually being Tales of Eternia (released in Europe on PSP, and that's region-free). There is an actual Tales of Destiny 2 (sequal), only available in Japanese.

Don't skip Legendia. Its good!

As for Symphonia, its good, as long as you don't play Abyss or Vesperia before it.

Abyss is the best Tales game.