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I think that the key to good political play is to allow (and encourage) one or more of the PCs to have political goals of their own. Rather than just doing "missions" for powerful NPC politicians. Although, that doesn't mean that the PCs have to have goals on the same scale as a king. For...

Depends what you mean by politics. I mean that the driving motivation for characters doing things is maintaining or improving themselves in some sort of power structure. And in that sense politics is pretty much the only reason NPCs do things, in my games, except for a few inevitable...

Yes, a warhorse, or whatever, should act however a trained animal of that type does. For that purpose, it shouldn't matter whether it was acquired via Summon Steed, or was purchased in the horse-market, or was rustled, or was rescued from a giant's larder.

Yes, this is the point of a familiar. However, just make sure that you not making it too good by misreading the rules. Outside combat, the familiar can only provide help to Ability Checks if the familiar can do the action himself (see PHB, page 175, Working Together). In combat, the Help...

This what I would do. Have the spawn gain a Life Force point per hit point of damage caused by the tentacles (or per 2 hit points damage; or whatever). Then, let the spawn take a Bonus Action to spend a Life Force point to either: Gain 1 Hit Dice of hit points (up to some maximum). Evolve a...

The angle isn't really relevant. Crawling and Climbing are different things. Hence why a typical baby is good at crawling, but rubbish at climbing. To address the main point, the Athlete feat already gives prone characters a bonus (easier to stand up than usual). So, I don't think anything more...

In my experience, (both as player and DM) this is very dependent on what the character is good at. Pretty much, when able to decide/make the choice, the player gets the PC to do the things that the PC is good at. So, PCs who are better at Investigation tend to try to use that more often than...

Absolutely. Also, beyond the issue of pure game mechanics that relate to the Intelligence Ability, there is the issue of the PC's character. In most games I have played in, NPCs (and other PCs) tend to react very differently to the ideas and directions of a stupid PC and a clever PC. It is also...

All depends on the individual players and the DM's game. In truth, there are no dump stats, just different characters.

First, I think it is important to realise that the PCs co-operating together and using spells and features to good effect is the game working as intended. You want to be very careful to discourage the players from devising good plans --- if whatever they do, they end up in a hard battle, then...

A PC who has sub-optimal statistics / game mechanics may still be optimal for fun / story. Flawed heroes are generally much more interesting than ideals. C.f. the characters in any book or film. A PC who has game mechanics flaws is the easiest flawed hero to make.

CON being a good choice for most PCs is simply a consequence of what most players anticipate the PCs are going to be doing. If the PCs are mostly blundering around in dark holes, getting stabbed by things, then there is obviously going to be a preference for hardy characters who have the best...

I would say that the general assumption is that someone proficient attacking with a quarterstaff is actually attacking with both ends. Because that is how you use a quarterstaff proficiently. It is just that this is normally represented in the game mechanics as a single attack roll. If you want...

I think that, in general, the idea actually is OK. It is a reasonably "clever" idea, although a bit degenerate if it is the only thing that he ever attempts. The main problem is it isn't that good, following the RAW, I think. This is the way that I think it should work: As others have noted...

Even if a combatant is wearing heavy armour, catching the edge of a shield in the face, or in a joint, is bad news. Especially, as it is liable to be a surprise.

Yes. It's a well balanced and maneovreable slab of solid with edges; plenty of scope for effectiveness. C.f. riot police.

I'm not really sure what the issue is. You can already use the Shove action to simply move the foe instead of knocking them Prone, and no-one actually forces you to bash an opponent you have knocked Prone. You can do something else, like knock another opponent Prone, or bash another standing...

Agree. Also, if the character happens to be proficient with a shield (e.g. a fighter), then it is reasonable to rule that her proficiency will count, anyway, if she makes an improvised shield bash attack (see discussion on Improvised Weapons at bottom of PHB pg 147).

Exactly. In the story that makes no sense. In the story, if the character really wants to succeed at something, he should be trying to use tactics/thinking etc. to get the Advantage and making a quick prayer to his gods for divine guidance. That's what we want the characters to do, because...

Good point. It actually seems like RAW that it wouldn't work at all on ability checks that arise from activities that take longer than a minute. It doesn't seem to allow you to just crazily cast the spell continuously for the activity period. If you are in the library researching for a week...