Lol what a great dilemma to have, choosing between two of the best knives under $60. Quality-wise, they are honestly both top notch, and there's a reason both are recommended so often. Both are lightweight, easy to carry, take a great edge, and are backed by fantastic companies. The skyline is much more conventionally attractive, and is a great "tactical gentleman's" folder. IMHO, the delica will be stronger because of the back lock, that is in Spyderco's heavy duty range, i.e. tested at over 100 inch-lbs at the lock per inch of blade length. That, plus the VG10 steel, causes me to carry the delica more often. Plus, I like the spyderhole over the flipper, the ergos are better for my hands, the handle is high-traction yet won't shred your pockets, and the multiple handle colors available make it even sweeter. I'm a huge delica fan, I had one in my pocket when I got married and when my son was born, and I'll probably be buried with one. The skyline is a good knife, nay, a great knife, but the Delica, especially the FFG version, is fantastic knife. That's my vote, though you really can't go wrong.
Edit: for the sharpener, if you want something easy, the Sharpmaker is tops IMHO, but it's somewhat pricey. A regulr Norton coarse/fine stone is cheaper, and will help develop your skills, but it is more work.