Nobody notices a good transmission calibration - but a bad one will infuriate the driver.
It also depends on what area of trans cal you are talking about clutch pressure control/shift quality or shift scheduling. The difference is significant.
There is a lot to do in terms of shift scheduling for emissions testing - but this is driven by a pinch each of common sense & science.
The shift scheduling for normal driveability means a lot of time in the car - and a lot of 'coaching' by 'experts'.
Pressure control/shift quality
Always at the behest of the quality guys who will want maximum durability from the mechanicals.
Always receiving 'coaching' on the presence of poor shifts etc
Both will mean a lot of time in the car, a lot of travel and a lot of fire fighting. Also some people struggle with the lack of 'ownership' of any tangible parts.
In terms of software MATLAB/Simulink are not difficult, especially when you are using them regularly and the application tool is most likely to be INCA, which takes no time at all to get the basics sorted.
If I were you I would go for it; its a varied & challenging job. Plus, if you don't like it you can always change with extra experience under your belt!