Battlefield Insight: My only note here is the range. You use 30 feet in a lot of places, which I think is a good and fine range. So why 15 feet here? I think its forces your allies too tightly to you, and it just adds extra confusion (oh wait that ability was that 15 or 30 ft....um, let me look it up). I would just make 30 feet your core range for basically everything....its smoother, and its cooler.
I throw this out there, is there a strong reason it needs to be the attack action to refresh insight? As warlords seem like helper characters, I can see them often foregoing attacks to perform help actions and other less directly combative stuff. I don't see any balance reason off hand this couldn't be used with any action, I don't think it breaks anything.
Good point on the 30 feet thing! I'll take note of that for v5.
I use the Attack Action because you're either using the Attack Action to actually, ya know, attack people (thus causing the battlefield to change as you harm someone or cause someone to act different) or using it for a SHOUT (which also causes the battlefield to change). I felt like it made sense with the fluff. I didn't consider the help action because it felt like something that was subpar to your other ability but it's a good point... I guess there's no reason to not just say 'when you take a standard action'? Is there a specfic action you think would make it weird?
I guess it would also work if you pick up some cantrips? Would that be a problem or a good thing? I guess it would be a good thing...
I also kinda wanted there to be situations where you WOULD have to skip out on generating insight dice on your turn you know, and make it less automatic. Since it's modelled on the Rogue's sneak attack, there's a certain level of thinking involved in getting the maximum out of that class feature ya know?
Shouts: I would shift the prone power from Rise UP to MOVE. Technically getting up from prone is a form of movement, so a person should be able to do that using your MOVE shout. So I would add it there just to reinforce that you can, and remove it from Rise Up. I am a little loathe that you have shouts for three ability scores here. I see why....but that is just not something classes generally do. Classes generally have your main stat, and your secondary. Intelligence and Charisma both have long standing history with Warlords (and both make sense for the class), so I respect the inclusion of both. Wisdom feels like overkill and dilutes the class too much. I would consider maybe a subclass for the wisdom focused warlord, but remove this from your core.
They actually added a Wisdom Warlord later on in like Martial Power 2 I think? Anyway, it felt interesting to have a class where you secondary mental ability shapes a lot of the way you play the class, and it also felt odd to have INT and CHA but not WIS there as well since it's a good stat to have attached to good skills. I also kinda tried my best not to make it impossible to mix and match your specialty stat and subclasses. A lot of them, you'll see, synergize with specific presence and thus stat specialty better than other, but you can make interesting build by going against the grain. I also tried to make them good enough even if you don't have a good modifier in that specific stat that you would still use them when the opportunity arose. I just really like the 'mix and match' nature of the Warlock I guess.
Another thing is I had the idea for the three core shouts and obvious STRIKE! and RISE UP! have obvious INT and CHA connotation respectively, so that left MOVE! as the sort of weird third one (though I guess I could also see an argument for switching the attribute attached to STRIKE! and MOVE!)... I guess I could have one of them end up as a mix of both? Maybe the AC bonus in he MOVE! should ends up being INT+CHA so you can play a balanced Warlord? That was also a type of Warlord in 4e, the Ressourceful Warlord.
I put standing from prone in RISE UP because I felt it was too narrow a shout, and also because Prone is SORTA a condition, so the shout that lets you end a condition lets you end that one too. Also why I threw in the escape a grab thing.
I want to note how I like that Rise Up is similar but distinctive from the paladin save aura (I see far too often warlord classes just become paladin wannabes). Its not as protective as the paladin aura, but with the added flexibility that you can move to a target and give them the boost, compared with a paladin where you must be in the very tight aura to get the bonus. that's a solid differentiator.
Thanks!
Extra Attack: Move the note about the Insight Pool boost to a new ability (and I am happy you are boosting it, I think that's perfect for 5th level). Extra Attack is such a common and standard ability that I never read the text for it, I had no idea that was there on my first two reads. Keep your changes separate as its own thing, its cleaner that way and plays nicer with multiclassing.
Ooh! That's a good point. Thank you for that note.
Warlord Presence: This is WAY too much at 2nd level.... you already have a solid class before you introduce this, but this takes it over the top. I would move these ability to 6th, right now 6th has no meat in your class (it has only a ribbon right now), so I think this is a good place to put it. Even at 6th, I am a bit worried for some of these abilities. 8-9 temp Hp every round, ~+6 to AC, ~3 to all damage....those are some strong numbers. You may want to implement an insight cost for those boosts.
Oh lastly, you need to define how long the temporary hitpoints last.
How about I keep the bonus on iniative at 2nd level, but move the upgrade to Shouts to 6th?
The thing with Inspiring Presence is that I don't think RISE UP will come up that often unless people start dropping prone on purpose... okay yeah that would be abuseable.
As a default temp HP last until they're depleted or you take a long rest. I didn't feel the need to make them any shorter. Shepherd Druid can hand out temp HP twice after every short rest.
Continued Education: Its probably harmless enough, but I also question if it really belongs in this class. As written, this is not some cosmopolitan skill guy, he is a tactical general. It feels like you just want to give this guy some skill love because he's often smart and smart people should get skills, but that's just not how 5e works. As the old saying goes "a designer has achieved perfection, not when he has anything left to add, but when he has nothing left to take away". So I would just toss it, and see if the class feels like its missing something then.... my gut says it will look just fine.
Yeah Continued Education was a weird one. I just wanted SOMETHING that wasn't combat based and I couldn't think of anything better. Like I said, I was using the Rogue chassis so there was a non-combat feature at that level and I needed to have something on mine. If you got ANY inkling of an idea I'm all ears... I've been dying for some fresh perspective on stuff like this.
I've got a subclass in mind for a sort of Diplomat Warlord (I call it the Crimson Phoenix Herald, as it's from an ofshoot school of the White Raven school) that can make use of Insight Dice in social contexts, I think I'll give it the extra skills stuff.
Improved Insight: So confirming, we go from 1d6 base straight to 3d6....there is no ability that takes us to 2d6 base correct? That feels strange, I kept looking for one expecting to find it.
Ah yeah I couldn't figure out a good pacing for those improvements, or where exactly to fit them in the progression. Maybe I could just always have you start with half your Insight Dice maximum, rounded down, and not bother calling out those upgrades?
General: I like the feeling of this class, and I am generally pretty anti-warlord. There is some good stuff here, and I think the mechanics are well designed (the insight pool is a cool concept, the shouts work well, etc). Most of my feedback is tweaks, I don't think we need fundamentally changes here.
Thank you for the good words and thank you very much for your criticisms. You gave me plenty of stuff to think about and it's gonna be invaluable!