As stated prior, I had thoughts on these multiple medical situations this season. I know I made some early claims about charts/spreadsheets/laminatedlists/etc. but I'll condense some of it as more details (and questions) come available.
Thank you again, FP, for starting this topic.
Thank you also to those whom wished me well on my "day".

Now, To begin...
Overall, and to add to MB's comments, I believe Survivor Insider extrapolated on those med-evacs. Going on to state that all 3 med-evacs will be from the game. NOT after being voted out.

So this topic is to try to narrow down our multiple Medical Situations into 3 Medical Evacuations.

So, no better way that to introduce the characters, in the way of...

An introduction to 3+ Medics whom we will be spending the season getting to know. (Not real names)

Medic A (aka Aaron):

Seen all over this season. With castaways at camp and in the thick of things at the challenge.

Here is Aaron (in uniform) with Joe (@ Chanloh?)
... with Jennifer @ Totang
... and with Aubry (where he is wearing a t-shirt) (@ ?)

Medic B (aka Bruno):

Mostly seen in the med evac at the challenge caps. Balding with stubble beard.

Medic C (aka Carl):

Seen arriving with JP at Totang.
The blurry bits being Cydney, Jason and Scot.
Looking at the close-up, it appears as if a beard is visible on the person getting their hair braided.

This initially suggests the leg injury is either Darnell, Alecia or Jennifer. (Unless this is AFTER the swap, perhaps even after the merge.)

Medic D (aka Dave):

I'll get to him with the med evac caps as well. Longer hair.

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So...
Medic Aaron.
Pretty much at every medical situation teased this season.
However, his visit with Aubry is of intrigue to me because...
...just what is it that Aubry has in her hair?

It is not the blue one she's wearing here...


nor the red one seen here...

Is it a Totang Buff? Or is it her red hairband (not the one she starts the game wearing) with dirt and paint on it?

My thought is... Aubry is safe until, at least, after the swap.

Medic Aaron's visit with Joe is a bit concerning. But again, I believe Joe is either the first episode mercy boot or perhaps another, early mercy boot. He won't want to leave, medical won't want to take him, the tribe will have to vote him out.

Medic Aaron's visit with Jennifer, as FP stated above, coincides with Jennifer feeling pain and then requesting to see the medics.
Jennifer is holding her ear and complains of it hurting so bad.

The recent CBS tease has dropped a major hint in that 'a bug crawls into the ear of and causes pain for one of the survivors'.
Then, Medic Aaron shows up and pries the bug loose.

Does it effect her longevity?

Well, if the boot story is within the tease, then yes.

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Medic Aaron also visits a camp, at night. (Brightened to see back ground)

He has a bit of a consultation with JP, and while his ACTUAL "medical" decision is NOT revealed...

... someone appears to be getting ON the quit boat...

My thought...
Jason. Kyle. Sarg. We have yet to learn what name he will actually use during the game. Other than CBS has been using Jason.
If it's an indicator AT ALL (CBS is using his last name) it makes me believe JP will use his last name, which would seem to hint that JP has a bit of a "character crush" on Mr. Kyle "Sarg" Jason.

Jason has a VERY noticeable tank-top tan-line.

He also has bloodied bandages on his shoulders.

I tried my darndest to find a level of brightness/contrast/color level that would BEST highlight why I think it is Jason.
ala...

I see the bandage on his right shoulder, I also see the noticeable tank-top tan line on his back. What I don't see is his boxer shorts, nor his actual tank-top. This most likely happens after bathing suits are delivered anyways but I also don't seem to see and tat's. So...
Well? Maybe?

On any hand, whether or not Medic Aaron actually says the male castaway needs to be removed or not... If there are indeed three med-evacs this season, this 'quit-boat' situation looks likely to be one of them.

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Meanwhile, Medic Carl is visiting Totang and sees someone there. It seems he's there to investigate the leg injury that is becoming infected.
The shorts are what will ultimately give it away for us as to who it is.
For the close-up...

Don't mean to place the wound in such a light BUT, the shorts are what we're looking at.
Those shorts are blue/turquoise/peach/white and appear to be of synthetic material.

Currently, no one's shorts match those.
Including Tai's blue/white/red cotton shorts...

Sorry, FP.

So... that suggests that THAT medical visit is not until AFTER bathing suits are given out. (Circa episode 3?)
And BOTH Darnell and Tai or even Peter could be our suspect with the leg injury.

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The Med Evac

All this hulabuloo happens at a challenge. Noticed because of the abundant shots of challenge equipment throughout and the fact that some players seem to be still in motion as JP calls for the Med-Evac.

Here are my thoughts on the progression.
Someone, or multiple people, fall due to heat and exhaustion at a challenge.
Medic Bruno and Medic Aaron arrive at the site, (while Tai and Julia look on) with their briefcase of equipment. (Initially taking his blood pressure readings and asking him questions).
Medic Dave arrives and with him brings a small crew of assistants. Carrying in the SEG Chest, with the IV materials.
JP leans down to calm the victim. (Which I'm pretty sure is just Caleb.) Medic Aaron and Medic Bruno administering to the patient and Medic Dave holding the bag.

A bit of image play... closeups and color flourishes to play with the eye

Aaron's hair matches up almost perfectly as Medic Bruno leans out from behind Medic Aaron.
The SEG-chest is being carried in, and then is open lidded behind JP as he leans over the patient.
Medic Dave is most likely the one holding the IV bag and the line is visible hanging down.

The "High" Blood Pressure reading.
A gloveless Medic Carlos inserts the catheter into the patient. While Medic Aaron looms in the upper right corner.
The shade has now been put up, the IV line visible. Medic Bruno appears to be opening/checking it. While Julia, another female and another person look upon the scene.

JP calls for the end of the challenge.
The Evacuation Copter arrives.
Assistants get the stretcher (from the chopper) and bring it to the patient.

Defintely a Med-Evac.
There may be multiple exhaustion sufferers, but Caleb will be the Med-Evac. IV bags, med-evac choppers, stretchers, these are all things that difinitively point to "Out of the Game" prior to TC.

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While all of this points to The Quit Boat (Jason) and The Challenge Med-Evac (Caleb) as 2 of the 3 evacuations, there is still the third.
All people mentioned before are suspect: Jennifer and her earworm, Joe and his exhaustion, Aubry and her looks of disdain, whomever of Peter, Tai or Darnell and their festering wound.

Considering MB's words carefully..."we had three evacuations, the most ever in a season. It was the humidity, cuts, people getting infected and then trying so hard on the challenges."
To me, this excludes Jennifer and Aubry. Joe could be down because of exhaustion. But I'm thinking the leg wound is our third med-evac.

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Now I just gotta hit 'post message'.

Do it.

Hit it...