The 5-foot square that a Medium orc
commands cannot be passed through by other
Medium creatures unless the orc allows them to.
I like this phrasing. There are allies you may want to block (eg: charmed ally, or clashing personalities that both want to claim the "best" spot), and enemies you may want to let through (draw into a trap, or just allow to escape). This is more likely to come up in non-combat turn-based action.
Likewise, the space determines the limit to the
number of creatures that can surround it; the orc
can be surrounded by a maximum of 8 Medium
creatures, or 4 Large creatures.
This, combined with the table, is slightly confusing. Having a medium creature surrounded by 4 large creatures makes sense. Geometrically, you can surround a 5'x5' block with 4 10'x10' blocks. However the table shows that tiny creatures (2.5'x2.5') can be surrounded by 8 creatures, and that only makes sense if it was surrounded by 8 tiny creatures. Medium creatures would have the same geometry relative to tiny creatures as large creatures have to medium, and thus only 4 should fit.
That in turn implies that the table is showing how many of the same-sized creature can surround a given creature, but that doesn't make sense when you get to larger creatures, where it looks like you're putting medium creatures around large+ creatures.
So, please clarify what size "surrounding" creatures are, relative to the "surrounded" creatures, on the table, and verify that the numbers are correct for your methodology.
If you are knocked prone, you make a DC 10
Dexterity saving throw or fall off prone in a
space adjacent to the creature you’re riding.
Awkward phrasing. "fall off prone" should probably just be "fall prone", or "fall off, and land prone".
If you’re riding another creature that you have
control of, you use its Speed instead of your own.
Remember that mounting or dismounting costs half
your Speed when choosing to move after you’ve
jumped onto or off the creature.
Suppose you have 30' move speed, and you mount a horse with 40' move speed. Mounting uses half your speed (15'). When you ride the horse from that point on, do you have 20' (half the horse's speed) or 25' (40' - 15') of movement remaining?
You can also drop prone as a reaction
to being targeted by a ranged attack you can see.
Nice.
While you are prone: Your only movement option is to crawl
(every 1 foot of movement while crawling
costs 1 extra foot) until you stand up.
Can you crawl into a body of water and switch to a swim speed? Is that affected by a 'prone' state? What happens if you get knocked off a pier and land in a lake? Are you considered prone, and have to spend half your movement to reorient yourself before you can start swimming?
Attacking From Above - If you are at least 5 feet above your target and you
aren’t grappled or restrained, you gain an expertise
die on melee attack rolls made against it.
This doesn't really make sense, for melee attacks. Are you directly above, like falling down on the target? In that case, sure. But otherwise it feels like you're adding 5' of range, which mostly means you can't hit the target, or at least would be disadvantaged, similar to if you were 10' away and attacking a prone target.
As long as neither you nor
your ally move, your passive Perception is increased
by 2 until either the start of your next turn or when
one of you moves.
Saying it ends when one of you moves is redundant with saying that you only get the benefit as long as neither of you move.
Flanking - When you and an ally are on direct opposite sides
of a target, you gain an expertise die on your actions
against that target. You and your ally cannot flank
for one another if either of you are incapacitated.
Can you clarify what "opposite sides" means when you're trying to flank a large+ creature? Does a line between the two attackers have to pass through the center of the creature's area, or does it merely have to pass through two opposite edges?
Half cover provides you with a
+2 bonus to AC, saving throws, and ability checks
made to hide.
It's nice that cover provides bonuses to attempts to hide.
Misc:
Love the environment stuff. Love the countdown. Appreciate the simplification of multiple summoned creatures.
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