The lower end of the Skylakes (the Us, Ss and Ts) will likely launch first. The Intel roadmaps show Skylake's release being stretched out from Q3 2015 to Q1 2016; I'm not expecting Skylake K (the over-clockable i5 6600K and i7 6700K) to drop before Christmas.
R9 3xx cards from AMD are coming around the end of June 2015, as is the GTX 980ti (that'll be out of your price bracket though). Depending on performance and price of AMD's cards this might see price-drops by nVidia.