No one knows. Everyone learns differently. That said, the study plans were drawn up with just your question in mind, so you should at least take a look at them (Learn in the top green ribbon, then Study Plans). IM Danny Rensch's Live Video sessions are a great way to see how a titled player thinks. The Chess Mentor courses on tactics are a great way to learn all the tactical motifs without time pressure. Of course there is time pressure in chess so you should test your self occasionally on the Tactics Trainer. To get really good you have to immerse yourself in chess culture, but the good news is you can make lots of improvement with a lesser commitment. Oh, and something Heisman emphasizes is that studying chess has to be fun or you won't stick to it. So run around like a kid in a candy store for awhile and just try anything and everything you're interested in. You'll settle down eventually. Good luck.
Improving with Diamond
A Diammond membership will give you access to a number of tools and interesting features to help you improve. You might find that very useful, especially if you are mostly an internet-based player.
It really depend on your needs. Some people can do more with less. Others want to have access to everything that might potentially improve their play.
Also, it might seems irrelevant at first but by buying a membership you're contributing to make chess.com a better place. You're helping these guys pay their bills and maintain this website that we all love to play on. So, if you have money to spend, than go for it.

Throwing around money alone without any discipline won't work. Its like quitting smoking. You have to want to become a better chess player. But as long as you have the money, start by reading this. We will grade your assignments on a weekly basis http://www.chess.com/forum/search?keyword=study+plans

Oooh
We're no strangers to love
You know the rules and so do I
A full commitment's what I'm thinking of
You wouldn't get this from any other guy
I just wanna tell you how I'm feeling
Gotta make you understand
Never gonna give you up
Never gonna let you down
Never gonna run around and desert you
Never gonna make you cry
Never gonna say goodbye
Never gonna tell a lie and hurt you
We've known each other for so long
Your heart's been aching, but you're too shy to say it
Inside, we both know what's been going on
We know the game and we're gonna play it
And if you ask me how I'm feeling
Don't tell me you're too blind to see
Never gonna give you up
Never gonna let you down
Never gonna run around and desert you
Never gonna make you cry
Never gonna say goodbye
Never gonna tell a lie and hurt you
Never gonna give you up
Never gonna let you down
Never gonna run around and desert you
Never gonna make you cry
Never gonna say goodbye
Never gonna tell a lie and hurt you
(Ooh, give you up)
(Ooh, give you up)
Never gonna give, never gonna give
(Give you up)
Never gonna give, never gonna give
(Give you up)
We've known each other for so long
Your heart's been aching, but you're too shy to say it
Inside, we both know what's been going on
We know the game and we're gonna play it
I just wanna tell you how I'm feeling
Gotta make you understand
Never gonna give you up
Never gonna let you down
Never gonna run around and desert you
Never gonna make you cry
Never gonna say goodbye
Never gonna tell a lie and hurt you
Never gonna give you up
Never gonna let you down
Never gonna run around and desert you
Never gonna make you cry
Never gonna say goodbye
Never gonna tell a lie and hurt you
Never gonna give you up
Never gonna let you down
Never gonna run around and desert you
Never gonna make you cry
Never gonna say goodbye
Never gonna tell a lie and hurt you

I do want to become a better chess player. That's the sole reason behind buying Diamond, and after looking through the tools available I'm just wondering how to go about learning. I learn best by doing and then seeing for myself, having that "AHA, so that's what's going on here kinda deal." I'm very dedicated to hobbies O enjoy (pool, and chess) and I absolutely dedicate myself to improving my game however I can.

analyze your own games, find errors, eliminate them
watch videos, get ideas, implement them
take a break for a few days
get it all started again
thats how i improve

This is a bit off the main topic, but I personally think Platinum is good enough, diamond seems a bit too expensive for just a few extra things (50 dollars)!!!!
I like to do lots of TT, to keep on grinding it into me
Then, I do live matches to see what happens
THEN I REPEAT
I got platinum for infinite tactics

Go over your games using this process, also go over Capablanca games using this process. --- http://www.chess.com/blog/bobbymac310

I was born with absolutely no talent at all for playing this game. There are many things I'm very good at but chess is not one of them. Plus I started playing chess 18 months ago and I'm 54 years old. I'm certainly not a young man anymore with a fresh mind. In my case I probably would have given up trying to learn to play chess awhile ago if I was not a diamond member. For a lousy hundred bucks I'm entitled to unlimited use of whatever I want to use and this has kept up my interest. And the more I use this site, the more I improve, and the higher my interest gets. I'm constantly on this site and totally hooked on the game now. If I had decided to only use chess books, I'm sure I would have quit from boredom by now.

Hey everybody - I'm wondering what's the best way to actually learn proper chess with Diamond benefits?
I'm only a 1200 ELO in Blitz, and 1400 in turn based, but I'd like to improve both. When I watch video commentary matches I don't understand a lot of what is going on until the commentator mentions something then it seems so clear.
I'd like to learn more about chess and get past these hurdles. So, what's the best way to learn proper/good/whatever word you want to choose chess with Diamond benefits?
I like the Diamond features a lot. I haven't yet watched all of the available videos that are available, but the ones I did watch very usually very helpful and instructing. Then I really like the feature of chess problems. They're a good tool to get practice with. Interactive lessons are a big help for me as well. I am about 1200

The videos are instructive but I think not particulary the best feature for learning. The problem with the videos is that there is no real structure to them as a group. Many of the themes are very specific and beginners like us benefit less from listening to a GM talk about the various intricacies of one or another variant of a particular opening, then from studying general chess concepts (like pawn structures, controlling the center, opening principles, etc.) If you like to learn through videos, then a really good set of videos is the Killegar Chess overview of Nimzowich's "My System" - google it, its on youtube. I'm almost through it. I'd like to get the book and follow along with it.
That's not to say that there's no value at all to the videos on C.c. They're informative and interesting - They are good for some things. its just that watching them alone won't put beginners like us an a path to becoming experts IMHO. It's like watching football post game shows thinking you'll eventually learn enough from it to coach an NFL team :oP
Definitely, chess mentor is very good though. I upped my membership to diamond so I could do more than 5 lessons per day. I repeat the lessons a lot so 5 was a bit restrictive. Also, once you get really in to a course, having to stop after only 5 lessons is a drag! Right now I'm working on IM Rensch's course on light/dark square complexes - It's awesome...
So I'd day Chess Mentor, Tactics Trainer and analysing your own games. I use C.c's computer analysis to help with that after every long game. That's what I do anyway and Ièm by no means a 'good chess player' yet but I'm getting way better...
Hey everybody - I'm wondering what's the best way to actually learn proper chess with Diamond benefits?
I'm only a 1200 ELO in Blitz, and 1400 in turn based, but I'd like to improve both. When I watch video commentary matches I don't understand a lot of what is going on until the commentator mentions something then it seems so clear.
I'd like to learn more about chess and get past these hurdles. So, what's the best way to learn proper/good/whatever word you want to choose chess with Diamond benefits?