You have asked 2 questions here.
1. How do I get over that double? - Stock gearing is 14/50 (is that what you are running?) and looking at the picture of your friend going over the double, you should have no problem coming out of that corner in 2nd gear with a higher rate of speed and clearing it. If you are WFO and casing that, then your bike needs to be looked at. If you are running 14/50 and having problems getting over the double, put a 51 or 52 on the back, so you can either carry 3rd gear in the corner or have the ability to short shift into 3rd before the jump.
2. What gearing do I need for the desert? - You can not run the same gearing for the track and the desert. OW is a wide open area, so you should run a smaller sprocket out back. Depending on what you like to ride out there and how fast you want to go, depends on the gearing. If your gearing now is too short (meaning you are running out of gears too fast), then drop a couple teeth in the rear. Again if you are running stock gearing (14/50), go down to a 48 out back.
If you want to make gear changing from one place to the other easy, I would run 14/48 for desert and 13/48 for the track. All you would have to do is change the counter shaft without pulling the rear wheel and making a sprocket change. 13/48 would be close to a 14/51, just make sure you cut your chain to allow for the switching back and forth of the counter. I have an 03 YZ250 smoker and I run 14/46 when out in the dez and that gives me decent gearing for my needs. If I was racing dez on this scooter, I would probably go a couple more teeth smaller out back. If I am running in the trees, I will go back to stock and it works fine there for my needs.
I would not run a larger sprocket on the counter as that will take away from your bottom end and you will playing "fan the clutch" all day and replacing clutch plates oftend.
Hope this helps..