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At the end of season two,
Five is shot and is dying. He uses his ability to travel back in time a few minutes to before he was shot, and as a result "heals" his wounds.
This kinda flies in the face of what happens near the end of season one, beginning of season two though,
When Allison's vocal cords are injured and she loses the ability to speak. At the beginning of season two when she first arrives in the 1960's, she still cannot speak.
What's going on here?
If you watch the scene when it happens, it seems like (in my interpretation) that Five did two separate things with time.
First, he did something that I don't believe we've seen him do before. Normally when he time travels, he makes a portal and goes through it from what we've seen as viewers. This time, he appears to start off by reversing time around him, which appears to be a new use of his powers that we haven't seen yet.
During this time, it seems like everyone who was shot ends up back up, so he seems to reverse time to right about when the Handler comes in. As he does this, he is running across the room to a new portal that he seems to make as he's running. Based on the timing of events around him; by the time he reaches the portal, he should also no longer be shot. So he doesn't need to heal when he time travels a few more seconds back through the portal, because he already had reversed time to a point where he hadn't been shot.
That's how I interpreted it at least. The only assumption it requires is that Five was able to learn how to reverse time around him. To me, this seems like a fairly reasonable extension of his powers, and the way the scene is definitely implies that is what happened to me.
As we see right back in the first episode of Season 1, UA time travel can also replace the individual's physical body with their body at another point in their own timeline. Although the first time this is accidental, I assumed that in the example you mention he did it again on purpose. So he didn't heal so much as deliberately de-age his physical body back to a point before he got shot.
I don't remember them explicitly saying this, but we do have previous examples of UA time travel causing a physical change in the traveller and an explanation of how that happened, so I'd argue we could extrapolate from that.
(One argument against this interpretation however is that Five has to laboriously work out the mathematics required to jump on other occasions, and the calculations to do this intentionally should have required more preparation)
I noticed this discrepancy too, and just kinda put it down to inconsistent writing, but after reading your question I decided to rewatch the episode to doublecheck if there is anything there that might explain this, and I think I now realise the difference.
In all the previous time jumps Five took, he effectively ripped a 'hole' in spacetime and travelled through it, like opening a door and stepping through into another reality. This method of time travel also clearly changes the timeline itself (whether the original timeline still somehow exists somewhere/when as well, or is rewritten, is not shown, and irrelevant to the show as we, the viewers, experience it).
This is evidenced by the reality at the beginning of season 2 being moments before the beginning of WWIII, something that did not happen in the original timeline shown in season 1. Also, we saw the moon rip apart at the end of season 1, but we know this was not part of the original armageddon as it was still clearly in the sky when oldFive was wandering the wastelands for 45 years after armaggedon. The existence of both young- and oldFive in the same timeline fits with this as well - Five is quite literally ripping a hole in the fabric of reality and entering through it, and can even meet other versions of himself in the new timeline.
However, during season 2 episode 6, Five had a quite revealing talk with his father, where he discussed his time travel abilities and the problems he has with it. His father suggests he needs to take baby steps:
Start small. Seconds, not decades.
We have already seen that the children are still learning about their powers, and they are growing and maturing through use. Vanya is the obvious example of this, but we see it with Klaus as well, from just being able to see and hear the dead, he develops his powers to enable the dead to interact with the living world (Ben in particular). I believe what we see in the final episode of season 2 is Five learning a new trick, so to speak.
As he lies there dying, he remembers his father's words about seconds, not decades, and when he uses his power this time, it is shown on screen to be very different. This time, he didn't rip a hole in spacetime and travel through it. We actually see the other characters moving in reverse, as time itself is reversed. Five has taken his powers to a new level.
What I suspect is happening here is that Five is jumping back a only split second and reinhabiting his existing body each time, repeating this exercise multiple times until he has reached his goal.
He has effectively moved on from jumping himself through time to actually reversing time itself.
