We got the Tailgater in the spring of 2012 & found the same issue with dense tree cover.
I had some extra coax laying around from when I was in the cable TV field.
I made up a 150' length on a cord reel. That plus the 50' they give you & I am able to position the dish just about anywhere needed to get a signal.
Just a word of caution about the DISH month by month plan.
We discontinued our subscription at the end of Dec 2012.
We haven't been out yet this year. Got too much going on with the renovations around the house.
In June they started billing a $5 account "keep alive" fee.
I haven't had a chance to go back through the website but I don't remember seeing that when I signed up.
I'm sure it's buried in some fine print somewhere.
Dave, Judy & Daisy May
2010 Sierra 356RL
2011 Silverado 2500 4WD, LT, Ext Cab, LB
Duramax 6.6L V8 Turbo Diesel
Allison 1000 6-Speed Automatic Transmission