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Lots of good Questions Archpaladin. I'll answer what I can.
I played the main game through 6-7 times with different builds and alignments, with different consequences. I have not done a playthrough on the new Enhanced Edition, so I cannot tell you how the DLCs interact with the main game.
Also, there have been changes to the main game with the Enhanced Edition that might make any guides or advice obsolete (such as item rarity).
That Said, here are some pointers:
1. Any polarized (not True Neutral) alignment will have consequences to options, both in terms of Kingdom options and NPC interactions. The playable NPCs are all accessible for all alignments, though later in the game alignment differences will come into play with consequences.
2. There are no critical items in the game. There are lots of +X stat items, weapons and armor. It is hard to find EXACTLY the weapon and armor you want, but there are a lot of options - and the new EE is supposed to have better shopping selection.
3. The only must-have skill for the main PC (IMHO) is Persuasion. I also take Skill Focus Persuasion at First level for this reason. The #2 skill is Perception/Trickery for Traps, hidden doors/items and locks. I always have a "Spotty McRogue" Mercenary in my group with these two maxed out. From there, make sure your party has all skills covered - as they come up in game. The only skill I have NEVER seen needed is Use Magic Device.
4. Timers and quests are odd. The only way you run into trouble for this is if you do a kingdom thing that fast-forwards the clock 14-28 days, especially when close to the Season of Bloom Event that happens every chapter. The new EE is supposed to have a better documentation of when quests expire.
5. There are a handful of times when you will choose one NPC over another (their goals or urgent need of help are in direct conflict). No way around that.
6. There are some side-quests that you may find unsatisfying, (the Hellknight Quest and Val's Redemption come to mind) as they don't (IMHO) give you the options you should have. But that's a writing choice.
7. the game follows a strict timer of when events happen relative to each chapter, and you can plan for it. I usually quickly solve the main-quest of a chapter, then finish exploring/doing sidequests and doing kingdom setup/management last. This is because some Kingdom events force the clock forward, which can auto-fail quests. In addition, you'll want kingdom features that facilitate fast-travel, and plan your "quests" to minimize travel time.
In Summary, I've generally beaten the game and gotten the "best" ending (you have to do all the Curse Researches for this to work) multiple times, with multiple alignment/choices, so don't fret your Lawful tendencies.
Playing through the game 2-3 times honestly made it better for me, not sure if that is meaningful advice (you may not have the time or patience for that). It would take a thorough guide/walkthrough to explain all the details of the game and how best to manage your Kingdom/Adventuring time.