Do most tables allow grappled creatures to be moved to end a grapple?

My table is starting a new campaign soon and we'll be doing a zero session where we sort out which optional rules we'll be using.

The overwhelming majority of my experiences at tables has had DMs ignoring the concept of simply moving a grappled creature out of the reach of whatever's grappling it (either by grappling the grappled creature with an ally and dragging it away, or using the shove action, or a telekinetic shove, or a myriad of other ways to move targets). Example: a vampire grapples the fighter, the monk shoves the vampire (or grapples and drags the fighter away).

RAW, when a grappled creature becomes out of reach of the grappler, that's enough to end the grapple. The only other things that end it are: (1) the grappled creature using its action to end the grapple or (2) the grappler becoming incapacitated or (3) the grappler chooses to end the grapple.

Inevitably, I attempt to move my grappled buddy using a variety of methods... and the DM simply thinks it's not enough that you can just... do that. They add some kind of contest for the grappler to maintain its grip or they allow the grappler to simply move for free along with the thing they're grappling.

SO. I was curious how much of a thing this has been at all ya'lls tables. Do most DMs and groups add that layer to ending a grapple?

I think it's flavorful and adds tension; it doesn't even seem all that unreasonable. But I'm a little annoyed that the situation keeps coming up. Was curious if everyone else was running into it too.

I've never actually had this come up, but I feel like it should be more based on context. I don't see how shoving a Behir would get someone out of its grapple, but for a humanoid grappler, it would make more sense.

Quote from TieflingLew >>

Inevitably, I attempt to move my grappled buddy using a variety of methods... and the DM simply thinks it's not enough that you can just... do that. They add some kind of contest for the grappler to maintain its grip or they allow the grappler to simply move for free along with the thing they're grappling.

SO. I was curious how much of a thing this has been at all ya'lls tables. Do most DMs and groups add that layer to ending a grapple?

I think it's flavorful and adds tension; it doesn't even seem all that unreasonable. But I'm a little annoyed that the situation keeps coming up. Was curious if everyone else was running into it too.

 I usually do that as well, with some kind of check between the mover and the grappler. It makes no sense that a halfling wizard could Shove a goliath in the jaws of a T-rex and because their buddy decides to fail the save it automatically works to free the goliath. I do often give Adv/DisAdv depending on the situation though. An upcast Thunderwave spell is going to be more effective than a BA Telekinesis, using a Grapple + Shove is going to be more effective than a Shove alone etc....

I've never had this come up but I think it would depend on some conditions like what was grappling what. Shove also only works on something that is a size larger than you and two medium creatures, since they are holding each other, is larger than a Large creature. I imagine if I wanted to be a stickler for whatever reason then I'd give the grappling creature a Disadvantage on their Strength/Dexterity Save against the Push attempt since they are already struggling keeping someone grappled and certainly some creatures like a Roper wouldn't be able to be moved to end the grappling condition.

Quote from heydanseegil >>

I've never had this come up but I think it would depend on some conditions like what was grappling what. Shove also only works on something that is a size larger than you and two medium creatures, since they are holding each other, is larger than a Large creature. I imagine if I wanted to be a stickler for whatever reason then I'd give the grappling creature a Disadvantage on their Strength/Dexterity Save against the Push attempt since they are already struggling keeping someone grappled and certainly some creatures like a Roper wouldn't be able to be moved to end the grappling condition.

 You can run it how you want, but I wouldn't equate 2 medium creatures > 1 large creature. And you're really just trying to move one of them.

But, as was already pointed out, it's fairly unsatisfying for one PC to shove their ally (who is in the grip of a vampire or something), ally gladly chooses to fail their save, and...poof, the ally is moved out of the grapple's reach. On the one hand, that probably feels too easy; it was an auto-succeed. On the other, the PC had to expend one of their attacks to free their ally, which isn't nothing. But, I get it. RAW is kind of lacking in drama in this instance.

So far, anyway, it seems most tables are handling this case-by-case. Which is fine. 

The rule I tend to agree with most is: whatever the established escape mechanic is...is what anyone has to overcome using whatever method they come up with. Or, at least, that's the measuring stick for the action. 

So if the Roper is holding on to the party's wizard:
the wizard has to beat a str/dex save of 14 to escape (as described in the roper stat block)
so does the fighter trying to help him, no matter what method they're using (shove, Telekinesis spell, etc.)