It's not hard to start, it just never gets easier because there's always something more to learn. If you're comfortable on your X14 then give it a try. I did a downwinder on one, but at my weight and with geezer balance it was a disaster. Kathy Shipman did a run on one and really liked it, but she could do a downwinder on a 2X4,
No wind for the next week. The best bet is to look at Windfinder or some other long term wind forcasting and see what they say. Gorge wind is pretty predictable, it's driven by the pressure gradient which is easily measured.