Hello. I am rather new to this website and chess in general (excluding early childhood years losing to my grandfather). I am finding it rather difficult to win recently. I am currently experimenting with openings, strategies, positioning. What would your advice for improvement be? All criticism is appreciated :)

pretty hard I guess. Spent a month and got from 800-1000 so I guess maybe a few months..

Well level 900 is a beginner. No shame in that. I think 1400 as goal is a bit high for now. I would focus on 1000-1100 and then the milestone 1200.

In order to reach that I would start at right after the rules of chess. You know how to move the pieces, you know en passent (do you?), so you need to focus on common themes in tactics. Forks, pins, discovered attacks. Openings, strategy and positions are not what you need to focus on now, because you don't have the insight yet that is needed to succesfully apply these things. You can memorize any opening you want, but if you blunder your queen because you never noticed that fork or discovered attack that was coming, it won't help you at all.

So, tactics! Lots of them! And maybe a good beginner book. Start right after the basic rules.

A few months for 500 points, it's so hard

I recommend the book: Bobby Fischer Teaches Chess. It's an excellent book for beginners that teaches you how to see tactics and how to employ tactics in your games. The book has helped me boost my rating several hundred points. Also before you start learning oppenings, you need to figure out what kind of chess player you are (aggressive,positional, or defensive).

Basically you need to get to an ability where you score 75% against someone who scores 75% against someone who would score 66% against you now.

Focus on your thought process and basic tactics, mate in three at most for starters.  It's unfortunate that you get the fun part of chess study out of the way relatively early.  Spend a month on thought process, which involves asking about checks, captures, threats, if you can get away with leaving something en prise, and if not protect or exchange the piece.  After that study basic positional elements such as weak pawns and squares (especially), color complexes, and dynamic compensation.  You have to know what goals to have in chess and know what strengths and weaknesses are. 

How hard would it be to bump my ELO from 900 to 1400.

You'll have to learn all the basics and be familiar with all the tactical themes (there aren't that many, fork, pin, skewer, etc).  And then of course practice applying all of this in real games.  Lots of practice.  I'd give it at least a year.  Depending on how often and hard you practice could be more (multiple years), could be less.

It helps a lot to find a local club where a stronger player can act as a friend (or coach) and you can learn a lot that way.  Books and tournaments are good too.  Blitz isn't going to teach you anything unless you review your losses.  And even then it's just blitz so mostly it's going to be "I was low on time and didn't see I was going to lose that piece / get checkmated" which isn't much of a lesson.

Hey Scott.  I am asumming you are not kidding.  Now, would you mind explaning yourself.

To the OP, depending on skills and time devoted to practice what waffllemaster mentioned you could potentially be done in one year, maybe.  Cheers.

Did you stop playing Waffle?  You've been 1962 forever .

What do you typically score against your opponent's that you defeat ?

I think a wafflemaster is about right. Expect at least a year of hard work. Study tactics and endgames and you'll make it.

Haha, I guess I could lose some games and have the blitz rating take over :p  I don't want to play bullet anymore.  Maybe I could try and up the blitz to 2000.  Hard for me to not play 50 blitz games in one sitting and right now I'm trying to actually study some chess instead of goofing off with blitz.