If you put it in the back of your pickup, lay it down on it's back. Laying it down on it's side would have too many stress points in my opinion.
On loading it yourself, you might have a difficult time there. I personally use a small 4' x 6' utility trailer myself. I lay down a mover's blanket in the bottom, lay the FEC on that and then just slide it in. It then gets covered with another mover's blanket and then a tarp which is bungied down. I also put a cinch strap on the fec to keep it in place.
If you consider a utility trailer, get one with a wooden floor in it instead of a expanded metal floor. Easier to get in. I think I paid $500 for my trailer over three years ago and it is still going strong.
On the rain issue, keep it well covered. And it probably would not to put a plastic bag over the electronics before putting it in the truck.
Hope this helps.