This is why you should look the under vinyl siding at the end of a gutter, if possible.
You mean where the kick out needs to go, which I always recommend, regardless if siding substructure is evaluated or not
Correct
Siding should be 1.5 to 2" higher than the roof decking, Step flashing under each shingle. Kickout or diverter flashing at the end.
I see a kickout at the roof line. Something else is going on like improper building wrap installation or missing flashing tape in that area.
There is a kickout there, yes, but the angle is so closed that it will hold more than deflect.
Needs to be bent outward more.
I guess I’m so used to never seeing them, I just assumed 
You think ice will backup there?
As well, I see not step flashing.
Good point Joshua.
Looking for what is missing is important.
The correct terminology is diverter flashing.
It is the last part of the flashing assembly.
In the images below, there are 3 missing and incorrectly installed components.
Three trades put these defects in place. IE: The builder’s responsibility.
1: The housewrap installer should have installed a thick flashing detail at Window, Wall abuts, and roofing deck transitions. That deck should not be incontact with the dormer.
2: The siding company should have maintained siding clearance at the roof deck dormer wall abut transition.
3: The roofer should have installed step flashings and lastly the diverter flashing. Even if there is no gutter works.
Look at the staining atop the siding at the butt locks.
Likely fungus and mildew. Moisture allows this.
See/observe similar staining, be suspect and investigate. Observe, measure,record.
Kickout is a poorly homemade piece of crap! (Improper). That one little detail can and does cause a lot more damage than most peoples think!
**Building Codes **
Installers need to be aware of building code requirements in the geographic areas where they are installing, and how the codes relate to the instructions given in this manual and by the siding manufacturer. The requirements of local building codes must always be observed, because they represent the legal requirements for an installation in a given jurisdiction.
That was taken from the VSI Manual.
The 1/2" per VSI is stated as a minimum.
In snow country, it is a standard to keep it up at least 1" of the shingles.
The J-molding nails, at 1/2" would put the nail penetration though the step flashing 1" above the roof.
Now unless you like to have holes in your flashing that low, I would suggest keeping your side wall siding at least 1" to 1&1/2" above the roof surface. Even more so for other types of sidings.
Also I will not be cussing the Contractor that set the J-Molding on the roof shingles when it is time to replace them. 
Good info, Marcel. 