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The [grappled] condition also ends if an effect removes the grappled creature from the reach of the grappler...
What's stopping the grapplee from shoving the grappler?
I've read that you can shove a grappled opponent to make them prone. Can the grapplee shove the grappler prone?
Nothing stops a grappled creature from shoving.
"Grappled" zeroes out your speed, and that's it. (PHB p.290, "Appendix A: Conditions")
However, this may not break the grapple.
As you've quoted, the effect ends if the grappler's reach is exceeded. On a successful shove you can either knock your target prone or push them 5' away (PHB pp.195-196, "Shoving a Creature").
Knocking the grappler prone doesn't--by itself--move you out of the grappler's reach. Shoving the grappler 5' is... uncertain.
The one definite case I can think of (just for fun):
Summary: this sounds like an excellent space for a ruling, leading to a house rule.
Nothing stops a grappled creature from shoving.
same as above
This will break the grapple of a 5' reach.
In grid-world even when grappled creatures are at a 5' "distance" because, as @daze413 rightly points out, grappling doesn't move one into the same square.
The shove then moves the grappler 5' farther away, exceeding a 5' reach. So: yes, in grid-world the equation is
grappled + 5' shove = 10' separation
Yes, you can generally shove your way out of a grapple
If a grappler can't reach their target, the grapple ends. If you shove someone 5' away, they won't be able to reach you anymore and the grapple will end. However, if their reach is larger than 5' they may be able to maintain the grapple on you (e.g. larger creatures).
I'm not aware of any rules RAW that would cause being prone to break a grapple. In fact, you might want to shove someone you've grappled prone so that he can't get up. This is more powerful for the grappler than the grapplee, since the grapplee has 0 movement and can't get up, but either character can do it.
From a game mechanics perspective, the question asks whether a creature can get a "two for one" outcome from the same opposed Strength/Dexterity check (a single die roll): does that one roll both accomplish the Shove and Escape from the Grapple action? This might run afoul of the action economy (which is slightly skewed in favor of the grappler).
The Grapple and the Shove are both considered a special melee attack, a subset of the Attack Action. Escaping a Grapple requires an action. (Basic Rules p. 74). Taking an action replaces using the attack action in most cases. Shove, Grapple, and Escape Grapple are opposed Strength/Dexterity checks.
The rules on Grappling and Escaping Grapples were not written symmetrically. Grapple is a special attack action, but breaking a grapple is not a special attack action, it is an action. (Note: a ruling could be to make the escape a special attack action as well, but that may not resolve the other issues involved).
Opposed Strength/Dexterity Check 1: Escape Grapple. (Basic Rules p. 74)
A grappled creature can use its action to escape. To do so, it must succeed on a Strength (Athletics) or Dexterity (Acrobatics) check contested by your Strength (Athletics) check.
Using the Attack action, you can make a special melee attack to shove a creature, either to knock it prone or push it away from you. If you’re able to make multiple attacks with the Attack action, this attack replaces one of them. The target must be no more than one size larger than you and must be within your reach. Instead of making an attack roll, you make a Strength (Athletics) check contested by the target’s Strength (Athletics) or Dexterity (Acrobatics) check (the target chooses the ability to use). If you win the contest, you either knock the target prone or push it 5 feet away from you. Shoving a Creature.
If the distance between combatants is assumed to be some number greater than zero, then adding 5' to that makes the distance greater than 5' and the conditions for breaking the Grapple have been met for creatures with a reach of 5' or less. For creatures with a reach of 10' or more, it would not appear to suffice.
If the distance between grappled combatants is assumed to be zero, since they are in physical contact, then the shove by itself cannot generate enough space to break the grapple.
Because the rules as they stand now demand slightly more to break the grapple -- requiring an action versus a special attack action -- then the opposed strength check necessary to break a grapple is the Escape Grapple Action.
Make the Grapple Escape the equivalent of Grapple or Shove, a special attack action, and fit it into the action economy. If the attendant ruling on distance is that the two creatures begin at a distance greater than 0 from each other you'd get the two for one feature as a byproduct of the rules overlapping.
Use a Shove to break a grapple as a special attack action in lieu of Escape Grapple (they are both opposed strength checks) so that it does not impose the same penalty on the grapplee of using an action. (Creatures having multiple attack actions would be more able to exploit escaping a grapple). This could be substituted in for the "prone" option of a Shove. A house rule along these lines should be closer to a balanced action economy.
Update: I have adopted this alternate approach in the shared world my brother and I DM in; this adds a slight benefit to martial characters like Fighters, Barbarians, Paladins, Monks, and Rangers for getting out of a grapple once they get to level 5 (and the College of Valor Bard at 6).
I'm surprised no one suggested that the shove action while grappled would move both of you 5ft in the direction shoved.
Since they are holding onto you and you shove them they simply bring you with them into their new space and it's technically not your movement but a side effect of your action and their hold on you. Not having movement doesn't make you immovable.
To address all of your points
(1) What's stopping the grapplee from shoving the grappler?
(2) I've read that you can shove a grappled opponent to make them prone. Can the grapplee shove the grappler prone?
Question 1: Nothing is stopping them.
Question 2: Yes but that won't end the grapple. There is no indication that the creature being grappled goes prone per RaW too, but I'd probably call for some sort of contest to remain standing in my game.
Implied question 3: "Does shoving them 5 ft away break the grapple?" Yes but only as RaI, not necessarily RaW. Shoving a creature is clearly meant to move a character out of reach. Otherwise it's not really useful at all.
... you can make a special melee attack to shove a creature, either to knock it prone or push it away from you... you either knock the target prone or push it 5 feet away from you. (Shoving a Creature, Basic Rules)
It says you move them "5 feet away from you", so a strict reading could say if they were 3ft away, you only move them 2ft and if they were 6 inches, you move them 4ft 6 in. Instead I believe that it's intended to be read as "5ft {from their previous position} away from you." As such even if they were right on top of you there would be some space, perhaps just millimeters, from you and so 5ft plus that space would put them out of reach.
