What sort of flies are you planning on chucking?
If you are tossing massive bunny leeches with lead eyes, then I'd go skagit all the way. That being said, I do not prefer the skagit system. It's highly functional, but I dislike casting it. I prefer skandi lines for all round function or a shortish belly spey line ~60ft. I also try not to use too many massive flies unless in murky/low vis conditions.
If you just want to get out and catch fish, go skagit. If you want to learn the basics of casting then get a short belly (~55-60ft) WF spey line. Also, unless you go skagit, do not try to cast weighted tips until you are comfortable with casting just a dry line. Trust me, weighted tips are a totally different deal and you'll need to hone your casting skills first.