I didn't read it all, because it was too long, and a lot of it was irrelevant - your online games here are enough.
(1) Your openings are fine - in fact, they're the strongest part of your game. You follow principled, positionally correct chess in the opening, and that's more than good enough for you.
(2) You need to work on your tactics. The positional advantage you often get in the opening becomes useless when tactics start happening. Dropping material to simple tactics and missing mates in 2 under no time pressure, as I've seen, is what will hold you back most. Buy "Back to Basics: Tactics", by Dan Heisman, and study it deeply. *Studying one book deeply is better than reading a ton of books superficially, which is AKA a waste of time*.
(3) Don't bother with any of the Silman books until you finish Heisman, which should take you at least a month or more, including applying what he says in your games. Specifically, the Amateur's mind and Imbalances are for 1600+ OTB.
(4) Pawn Power and My System are good books, although you should work on tactics more.
(5) Your goals are reasonable.
(6) You have more than enough resources online to get good at chess. Resources are totally fine.
(7) The biggest mistake that beginners, especially older players make, is getting a lot of useless information and not applying useful information in their games. You should focus on the tactics book, and apply all the stuff in your games. *If you can't apply a piece of knowledge directly in your games to get better results, that knowledge is worth 0*.
TLDR : Don't worry about "planning", "positional play", or "strategy" too much. Just focus on following the basic principles (that you're already following pretty nicely in the opening), and work on tactics, and you'll be on the way to 1600 pretty fast (which requires no more positional understanding than you already have, but a lot more tactical skill.) By pretty fast, I mean maybe 3 years max, if you do it right. This is pretty slow improvement, so it should be much faster.
My strength:
I am a former beginning, approaching intermediate player 24 years ago. Last USCF rating was/is 1271, with 32 rated games played I haven’t played in a tournament since 1993; other than some random pickup games with some friends who have never played tournaments themselves.
My History:
Prior to 1992 I knew how the pieces moved, but had no idea how to win at chess prior to meeting the high school chess coach. I had played some with my dad, who always beat me so I had that level of interest of learning how to play. Our High School was small (I graduated with 98) so it was not a developed club, but one that would often times not have a team compete. Since I had some level of interest he got me into playing, and we ended up with a club of 4 players to have a team.
Our first qualifying tournament for the state tournament, were my first rated matches in April 1992.
I don’t remember the details of that tournament but my provisional rating after that tournament was 1188. The state championships, which we somehow barely qualified to participate I won 1 and lost 4, and my rating dropped to 1140. Then that year we went to the national scholastic high school tournament in Lexington in May, 1992. I went 3-0-4 and my rating went up to 1237. I finished 69th in the U1300 division. While we were there I bought my first chess set and my first chess book. It was End Game Course by Bruce Pandolfini.
The following year, I became first chair (yes, our team was pretty weak) with that rating. I read the book on the bus ride home from school and become strong enough to beat my chess coach (I would estimate his rating at that time to be around 1150 – 1200). The regional qualifier was eliminated and all teams went to the state tournament. Playing first board, I got beat badly again, going 1-4-0. My rating dropped to 1213. I went to the national chess tournament alone, since it was in Dallas and the team couldn’t drive. I went 4-0-3 and ended up 26th in the u1300 division. My rating as mentioned earlier went up to 1271.
My time away:
Graduating and going to college and then career etc caused me to put chess down, and until I watched Netflix documentary of Magnus Carlsen, I hadn’t even thought about playing serious. I just played when someone would bring it up and I would pack my old chess board. Now I am ready to devote myself to some unknown degree due to loss of interest in other hobbies. I lost all of my chess stuff (books, notation pad, etc. except my vinyl board and wood pieces I bought in Lexington.
Current status:
I am rusty but playing some rapid games on here and a few OTB with a friend of similar strength I am getting the dust off my game. I also reached out and contacted the local chess club, and will be attending a meeting very soon. So I look like a valuable member I bought a clock, a bag, and a new notation pad, since my old one was lost. I do the daily puzzle and the 5 tactics problems daily.
My self critique:
My opening is weak and I use most of my time getting through it without a compromised position as best I can. If I can gain a material advantage I attempt to shorten the middlegame and get to the end game that I feel confident because of my reading of the end game book.
My attacks seem predicated on my opponent making a mistake. I can win when he or she doesn’t make a blunder and if simple combinations are available. My opening lack of knowledge seems to lead to an absence of a plan.
My plan to begin improving:
In addition to going to the local club I have ordered the following based on other thread research:
The Amateur’s mind: Turning Chess Misconceptions into Chess Mastery - Silman
How to Reassess Your Chess: Chess Mastery Through Chess Imbalances - Silman
Silman’s Complete Endgame Course: From Beginning to Master
I also got Back to Basics: Openings - Carsten Hansen
Based on further reading, I need to practice tactics and since I am in the ordering mood I have the following in my cart but I haven’t purchased because I felt I needed some feedback.
The Ultimate Chess Puzzle Book – Emms
Chess: 5334 Problems, Combinations, and Games - Polgar
The Complete Chess workout: Train your brain with 1200 puzzles! - Palliser
My System (Chess Classics) - Nimzowich
Pawn Power in Chess – Hans Kmoch
I have about 15-20 hours a week to devote to study/online play
My Goal(s):
I would like to hit a 1400 by end of the year, and play in the rated tournaments to track my progress
Stretch goal (3-5 year) is to reach 1600, and be able to feel competent in all phases of the game.
My Questions:
Does my stated plan correlate to my strength, my history, and my current status?
If not, do you have a recommendation?
Is the advanced memberships on chess.com better investment than these books?
When I begin getting games OTB to analyze, is the website an adequate resource?
Other than a goal, what am I missing?
Thank you for any feedback,
Steve