That's what I do outside of combat. There isn't much point in not doing it, since the only "cost" of doing things the official way is taking a slightly longer short rest than normal, ie, taking two or three short rests in a row. I never track exact minutes anyways, so that's what I get with either system, and simply assuming that the clerical healing is used saves the trouble of saying that you're taking multiple short rests.
Honestly, its what I do with every encounter power used outside of an encounter. I figure you take "some time" to use it as much as you need, within reason.
And to answer Doctor Proctor's question, this is why.
I like short rests to be a literary convention. I like that they take an undetermined amount of time. I like how they break off the otherwise total focus on counting rounds, powers and such. And in that light, it doesn't make any sense to have "two short rests".
A short rest in itself just enough time for the defenders (in the next room, say) to prepare themselves, don their armor, and take their positions. It is a beautiful simplification. The point being:
don't worry about exactly how long your rest takes and how many rounds you need to heal up, because the timer is off, and your enemies will be ready for you regardless.
To me, the first thing about having a second short rest would be like saying right when a race is about to begin, everyone ready in their starting blocks, the referee raising the start pistol... "okay, just give me a minute, I'm not really done after all".
My other and more central concern is this:
If we agree taking two short rests does not change anything, then we agree there are no price attached to doing so. And D&D is about choices having costs. Okay, so what about if the second short rest does have a price (in how the defenders get reinforcements, prepare better fortifications etc)?
But this would then negate the main point of the short rest as a convention. No longer would it be true that a short rest is what separates encounters, and that a short rest is just enough time for the defenders...
...because now we introduce the new concept of the "double short rest" where the defenders get to prepare themselves
more.
And this to me is a sad path to go down, because what I see at the end of it is the return of the minute-by-minute obsession.
Taking more than *a* short rest to me says you haven't fully grasped and embraced the notion of the short rest as the definition of "just enough time". It says to me you're really clinging to the notion that time passes minute by minute, and that "surely" ten minutes is better than five.
But the brilliance of the short rest idea to me was the idea to break off from minutes and seconds and instead say it's enough to heal you up but also enough for the defenders to get into the positions that the adventure designer have chosen.
Thus creating the most fun encounter, instead of getting bogged down in realism issues like "how did that guard have time to wake up, get his weapon, and take up position in the ballista tower?"
If you take a short rest, and the game is clearly geared towards you doing so, you accept the "social contract" where "if you get to heal, the enemy gets to prepare" - but with the understanding this preparation adds fun to the game by making the opposition 'just right' rather than the game having to worry about guards without their armor and shields etc. And in the end, this goes for player characters too: in essence, the game getting rid of the nightly ambushes where people are taken unawares, which in a gear-based game like D&D, is a disaster.
All good, in my view.
Again, being able and encouraged to sometimes take two short rests means to think in terms of several layers of enemy preparation. (Because otherwise the extra short rests are effectively free)
This to me is a (partial) surrender of the entire idea with short rests. Just as round-by-round healing would be a complete surrender, where "every round counts" and the DM is expected to run enemy preparations behind the scenes, also round by round; so that if the party heals up in 8 rounds instead of 11, that could mean some guards haven't exited their barracks yet (or whatever).
My solution is something I would have liked the designers to have the guts to add in as a standard rule because I believe it is better for the game for everybody.
My main objection is that currently the designers are selling a half-baked solution that isn't pure and does nottake the consequences of its own logic.
Hope this answers the question, DP, and that you didn't fall asleep when you read it...