Before I switched to dish a couple of months ago, I went down your path.
I have the 18" SD dish and can get it setup in less than 10 minutes.
I moved to the HD (with the power injector) as well, and as with the 18" round it took a while to get it working, the first time - adn the second time.
The hardest part is knowing what your skew needs to be. Also unlike the SD setup - which is you get the signal as high as you can and you're done - you have to get the signal as high as you can, then set the skew and it can (and did for me) throw off my signal strength.
What I found was it's a learning curve but if you're patient and you don't rush it, it's about a 20 minute time frame for me (the 3td and last time I did it).
FWIW, when I moved to dish, what I was pleasantly surprised was the technology they have integrated into their receivers - which Directv seems to have not kept up with.
One more thing. You don't have to move to dish to take it with you. you can purchase your own receiver (which you can't do with Directv) and connect it to whatever satellite dish you want (one that's designed for dish) and use it as you need it - leaving your DTV at home and using dish on the road.
I know. a pain, but you pays you go - and the satetllite dish is about the same as an 18" dish for directv. There are always options!
Hell.. if you're in a place with internet, you can stream what you have at home on your phone. No dish required on the road! :)
