If you send us your Skyline document and your mass spec data files we can try to figure out what is going on.
In Skyline you can use the menu item:
File > Share
to create a .zip file containing your Skyline document and supporting files including extracted chromatograms.
That Share Document dialog gives you the option of including the raw mass spec data files, or you could send them to use separately.
Files which are less than 50MB can be attached to these support requests.
You can always upload larger files here:
https://skyline.ms/files.url
I would also recommend looking at the Small Molecule Targets tutorial if you have not already:
https://skyline.ms/wiki/home/software/Skyline/page.view?name=tutorial_small_molecule
-- Nick