Just as an aside - and please don't take this as me being nasty - but game designers don't always make the best DMs. I wouldn't consider any of the game designer's calls on Twitter to be gospel if I were you.
Do not worry, i only look up to the official Sage Advice compendium for inspiration. I do not take RAW or anything as gospel. Rule 0 is have fun, Rule 1 is DM is the Final Judge.
And there are also clarifications in the official Sage Advice that are clearly sloppy and take a 180 turn on rules that are clearly written. Humans are fallible sadly. Or luckily?
Oh for the love of God.
Its a tree. It could be a Californian oak tree big enough to hide a T-Rex behind for all I know. The assumption is the 'tree' is big enough to hide behind.
Depends on if the Ogre is now observing him 'closely enough' or not.
If Yes: No hiding allowed.
If No: Hiding is OK
If maybe, but not clearly: Probably, but with disadvantage.
Whats the Ogre doing? Is he watching the Rogue 'closely enough'? Or did he ignore the Rogue and look away for a few seconds thinking the shot came from elsewhere?
The game assumes the Ogre is aware of the rogue as the attack is resolved, and generally remains alert to the rogue (watching him), but he may not be. Depends on the Ogre, and the situation.
Assuming no distractions from the Ogre, and only a handful of trees about, then I would rule no 're-hiding'. If the rogue was shooting in a forest from 150' away then I would rule re-hiding is OK.
I like how you are trying to justify your interpretation when the easy and most correct way out would have been "Because that's how i would rule as a DM, and that's how he does. They do not need to align".
The first part about hiding is that the DM dictates when you can hide. THIS IS CRUCIAL. And that's why you can keep saying how someone can go through a door and still be considered seen. Not because you are universally right. But because your interpretation is as valid as Mearls. Yet "let's try and rationalize everything even if Mearls has this thing where the basis is in complete opposition from mine".
I can't believe I'm getting involved in this mess, but here goes:
(sorry for the snip)
And that's it. I do not agree that the hiding section is poorly written - just awfully sparse. It gives a basic set of tools and establishes the "general" on which the DM HAS TO JUDGE, case by case. And we can argue how much we want that "see" actually means "see" or not. I prefer having my bases large and permitting than strict and unforgiving. I prefer to say "Yeah you can hide there, they cannot see you. They can see everywhere else tho. And it's not like they'll forget about you... do you really want to spend your action for that?" and let the player make the choice.
Also being strict ends up in situations like this...
He does indeed. But not due to being hidden. He gets advantage due to the invisible condition (see the back of the PHB for conditions). While he is not hidden from you, you cant see where his attacks are coming from and cant parry/ dodge them effectively.
If a wizard casts invisibility, he cant hide in the same turn and is not automatically hidden (despite being invisible). He can try the following turn to Hide (using his action) but until he successfully does so, he can be attacked normally (at disadvantage, while also immune to AoO and many spells which require a target 'you can see').
When actually what he meant to say is that "a Wizard that has no level in sorcerer or fighter or rogue or that has no other way to Hide as anything but an action and another 10 thousands other possible exceptions like being in a zone of silence in a completely empty space sinc ethe reason he can't hide is not because he can't but because he can't use another action, no matter what i think about the previous explanation about known position and whatnot."
A better approach to rulings is to be... i guess positive is the right word? You say "a Wizard that has just cast invisibility can hide as long as he can take the Hide action in some way or there's a situation that can make me think it's a good idea to allow it" as a DM and it's IMMEDIATELY clear to the player if there's something he can do about it. No need to create a thousand of exceptions and sub rules. The DM adjudicates on the spot.
For the hiding pillar thing: "Yes, you can hide there. Your pursuers are not stupid tho and you would have no way to flee from there if not in some place they can see. In one round they'll be there and they'll see you. And no, going in hiding and then attacking is not going to give you jack sheep. They expect to be fired upon."
All round better, does not cut options for your player if he wants to be dumb or if he has a brilliant idea that you have not thought about.
Overall, imho, simpler and more effective than a long list of no's and rules.
By the way, i prefer large and permissive. That's not really how i roll for everything tho. Ready actions is one of those places where i'm clear cut tyrannical.