First and foremost, almost every experienced player here will tell you to PLAY. And play A LOT. I would add that you should analyze every game after you have played it. How would you know if you are doing the right thing (opening/middlegame/end game/tactics) if you don't check your mistakes after every game you played? Books alone will not make you a strong player. Experience will. And there are a lot of experienced players hanging around in the game analysis forums that are always willing to lend a helping hand.
You are a diamond member. Make use of it and follow the Chess.com study plans. I would say do a mix of tactics trainer and tactics from books. After that end game study, add a bit of middle game into the mix and LASTLY openings. For openings I would recommend playing your favorite opening lines in Chess.com "themed tournaments". By knowing the basic ideas behind the moves, you get to "experiment" in these tourneys and gain a lot of experience.
I think you made a good choice in buying the "Reassess" book. Don't fall into the trap of buying many more books and end up reading none of them. See how serious you are about chess after a couple of months of study/play.
I'd like to start and say that after spending about a week or so, some lessons with the chess tutor from the website, and watching videos on openings, tactics, and theory, I was ablle to raise my rating by almost 200 by winning 11 out of my last 12 games. I'm no super beginner, I learned the main tactics as a youngster, but wasn't following a lot of the main concepts.
A friend from my chess club recommended 1001 brilliant sacrifices and combinatinos and I went ahead and got that with the 1001 brilliant checkmates. I have Silman's 4th edition of "how to reassess your chess" but it says on the back that it is intended for 1400's and above. I'm considering getting Tillman's "The Art of Chess analysis", but once again I don't know if it's too advanced for me or not. Should I just start with some basic opening books? I took a look through "The Fascinating King's Gambit" and found it a bit too dense, and unorganized. Tal's autobiography is something I picked up for fun. So I guess what I'm saying is what are the basic books I should be reading? Is the Silman still good? Should I go through the entire annotated games or start with the diagram? And yes I have the newest edition of "modern chess openings" for reference but I've been using the videos for openings.