I almost feel like this "Getting Into" stuff is going to become a recurring thing.  I've been gaming all my life but my interests have been relatively shallow.  I'm looking to expand them.  On that note, I desperately want to be an RPG gamer.  Whenever someone talks about an RPG with fondness I wish I could participate in the discussion.  I love sci-fi and fantasy novels.  I love deep stories.  I should love RPGs.  I buy them compulsively telling myself, "This time, you WILL finish this game."  But there are problems. 
 Firstly, in games like Dragon Age, Fallout 3, or Mass Effect, where skill points are assigned, I'm always worried I will mess up my character irreparably.  To calm myself I spend hours upon hours of time on the Internet researching character builds, usually while I sit at the main screen of the game the day I got it (as I am doing now with Mass Effect).  I am unable to make my own character decisions to suit my playstyle.  I research which characters to take along, what weapons to use, and about the long-term affects of dialouge choices.  Inevitably, I will stumble upon a spoiler for the game.  This ruins my experience, so why don't I just stop?  Well, I'm more afraid that the fun will be destroyed with a bad character than that it will be destroyed by a spoiler.
I've tried to play many Final Fantasies (I, III, IV, VI, VII, XII) but I end up quitting, probably from fatigue.  I like what I'm playing but 1) I die a lot, and 2) my  "OCD" kicks in.  I have literally restarted a Final Fantasy a good 10 hours in because I missed one sort-of-important-yet-optional item.  I look in every single corner for items and go through every dialouge sequence.  I know this is what a lot of people like about RPGs but to me it seems like a waste of my time.  The thought of putting 100 hours of my life into a game is a daunting thought.  Many a time I will restart an RPG because I feel like I'm "going too slowly".  When I go back to an RPG I haven't played for a while, I almost always restart again.  Stupid, I know.  All of my feelings are irrational, but I can't get over them.   I feel like this attitude could change but I need to be introduced to the experience gradually. 
The "RPGs" I have played through are every Pokemon game besides D/Pe/Pl, Mario and Luigi's Superstar Saga, and Paper Mario and the Thousand Year Door.  I watched the whole Endurance Run of Persona 4.  I think that's it but there are probably a few more.  I've had Chrono Trigger DS since release day and stopped at the place with the jungle-people-things.  I think I have almost beaten Crisis Core.  I'm loving my playthrough of Borderlands but fatigue's set in at about level 30.  I'm hoping to pick up Bowser's Inside Story soon and I am willing myself to finish Mass Effect and Fallout 3 this year (though I'm worried that when I start Fallout 3 I'll feel the need to restart, and my character's pretty built up).  My question is, good people of GiantBomb: 

What RPGs would you recommend for someone with my relationship with RPGs?  I'm looking for something not too intimidating, with a good story and characters, maybe a classic.  A game that lends itself to being the first (or next) step in becoming an RPG gamer.  Really, anything you loved yourself.  Also, some advice on how to handle my irrational antics would be nice.  Thanks!
 
Hopefully the rare person with the same dilemma as me can get something out of this discussion as well.

Oh, super easy: Nintendo RPGs are usually a good start, Earthbound included. I'd also recommend the original Final Fantasy and those DS Dragon Quest games.

Persona 4 fits all of your requirements except being a classic. That game is fucking amazing.

If you want JRPGs, I'd reccomend a lot of DS titles 
If you want WRPGs, I'd reccomend a lot of PC titles. 
 
So I need specifics.. and junk.

Give FFX a shot , it's much more linear than other FF's (except XIII) and it's a much more focused experience with barely any collection, choices or optional things before end-game. In addition the battle system is a more traditional turn-based format making it a bit more friendly and accommodating for new players. Plus, it looks good for an 8 year old game. 

" @InfiniteGeass: Well I watched the entire Endurance Run and I agree, one of the best games I ever... watched.  Should have mentioned that.  I picked up FES but it seems rather unapproachable compared to Persona 4.   I don't know if I could handle another 100 hours of Persona 4.  Thanks though. "

" @thecleric: JRPGs or WRPGs, QRPGS or LMNOPs, any good RPG.  I have so much fun with Nintendo RPGs and DS games in general, they're simple fun.  I don't know if I can get much more specific.  "

" @thecleric: JRPGs or WRPGs, QRPGS or LMNOPs, any good RPG.

Don't worry about spec-ing your characters so poorly that it cannot be fixed. Just go slow when picking skills or whatever and choose the ones that you think you will use. It's not that hard at all.

Just try not to worry so much, the developers and testing teams have your back.  It is extremely hard to end up with a character that just doesn't work nowadays - unless you go out of your way to do it, it just won't happen.  Mass Effect especially - I'm sure you could level up in Mass Effect with your eyes closed and you would still end up with a more than capable team.
 
Something like Dragon Age is a little more involved, but once you have a basic grasp of how a standard RPG party dynamic should work, levelling up your party members is nowhere near as intimidating as the level up screen might look at first glance.  Decide on your party structure (eg. Tank, Healer, Rogue, DPS), decide which character will perform which role and then exclusively focus on that one role when you are levelling them up.  As a rule, being a Jack of All Trades is not the ideal way to go in an RPG.
 
If your OCD is as bad as you say then you might be better off avoiding RPGs entirely.  I know that 'I must check every corner' feeling and it'll suck the fun right out of a game if you let it.  Have you considered trying a few adventure games?  They might suit you a little better - you can still get a solid story and characters but without that nagging "maybe I should have..." feeling, because generally speaking, you can only be right or wrong, and if you're advancing then you haven't missed anything.

• Final Fantasy X
• Lunar Silver Star Story Complete
• Star Ocean 2
• Wild Arms  2
• Skies of Arcadia
  

Your problem is your need to find everything and to know how your choices will affect the game.  What is cool about many RPG's is that your choices do affect the experience, and that as a result you will have a unique experience with whatever given RPG you play.  Take Fallout 3 for example.  There is an absurd amount of content in that game, and your choices always have direct impacts on the story and gameplay.  I would recommend that when you play it, you don't even try to find everything.  Just let the story carry you through the game, and let your actions and choices reflect what you want to take away from the game.  Don't try to look up the "right" answers on the internet; let yourself think about what you want to do.  Also, don't use a walkthrough.  I know which part you are talking about in Chrono Trigger, and you will ruin it for yourself if you know exactly what to do.  The feeling that that game manages to instill in the player -- that you are traveling through time and really affecting the course of future events -- is something that can only be understood if you achieve it on your own.  Obviously the Pokemon games are the exception to this rule.  They are designed so that the main goal is to find everything, but most RPG's aren't structured like that.  Basically, just enjoy each game for what it is, and don't think about what you may or may not be missing.

Maybe you just don't like RPG's.It doesn't make you a bad gamer if you don't. I personally can't stand them, but I know many who can't get enough. We're all different, you just gotta realise what games you're into, then get the most out of them possible.

Wow, you're really over thinking a lot of this stuff.  I never worry about character builds until the second run.  In fact, for me that's half the fun.  After I figure out how everything works in a game, I enjoy going back and trying it with my new found knowledge.  If there is one thing I've learned it's specialization is better than "jack-of-all-trades" most of the time.  Pick a few specific skills and work them heavily.  On occasion, you may need to place a few points in areas that are lacking, but for the majority, stick to areas that enhance your class.  Additionally, watch your hit-points and armor.  I generally place one into those areas (whatever they are called in the game) for every two that go toward combat skills.  I find it's better to be able to take a knock to the jaw more often than become a "glass cannon".  I have a tendency to die a lot, too in the early levels, but once I get over the hump, my strong health allows me to muster through most fights.    

" The thought of putting 100 hours of my life into a game is a daunting thought."

A couple of new DS RPGs are out this month that might be worth your time.  Sands of Destruction came out this past week, and Nintendo is publishing a Greek-themed RPG, Glory of Heracles, which comes out next week.

rpgs have turned into my favorite genre by far. Fire emblem and Baiten kaitos sorta started me into rpgs so i always recommend those first.. after watching the ER i started playing persona 3 FES and it is great (some things like fast travel in certain sections of maps is annoying) but i would highly recommend it still!

Personally, one of the simpler RPGs I've played, but one that I enjoyed quite a bit was Eternal Sonata. I wrote a review of it if you want to check it out.
 
As for your "issues." To combat the issue of continually starting over, I would simply try and stick with the one game until you make it all of the way through. I know that, personally, I don't want to put down a game like an RPG for a while because I may forget where I am in the story and feel the need to start over. Try your best to start a game and stick with it. At the same time, if you genuinely don't like a game, go ahead and put it down for good. If you feel compelled to complete a game out of obligation, you're not going to have fun and you're going to fatigue yourself with the entire genre.
 
As for the skill points issue: All I can say is, "relax." :) I understand what you're saying, but the likelihood of you screwing up a character so badly that the game is unplayable is slim to none, especially with more modern RPGs. There are a few general rules to follow: Always invest in at least some combat skills (you may want to play the whole game as a smooth-talking, mechanical genius, but it's not going to happen), try and focus your points into a few different areas (it's better to be good at a few things than mediocre at a lot), and if you have a party, try and bring along different types of characters (ie. close-quarters, ranged, engineer etc.). 
 
Lastly, remember that gaming is about having fun, and RPGs, specifically, are about carving your own story into the world presented to you. You could look online and try and find all of the "best" decisions and items, but at the end of the day, that's that person's experience with the game, not yours. If it weren't for making choices for yourself, then there would be no reason to play an RPG; you'd be better off playing a linear adventure game that guides you down one path and doesn't stress you out. Whatever decisions you make and actions you take are not "worse" or "better" than another person's. There is no "right" way to play an RPG; you simply have to make your own story out of it. Personally, I find RPGs to be so much fun because of the fact that you can inject yourself into the world, and try and make the best decisions that you can and then see how they turn out. Just like in real life, mistakes are part of the process and it's both the mistakes and good decisions that make the game your own. You take that away and you no longer are role-playing; you're just going through the motions.
 
Good luck.