I agree with the Dish Tech. Any connections are going to introduce signal loss to some degree. Several reports here show acceptable results nonetheless, but for best results I would use one clean cable from the receiver to the Tailgater.
That said, I'm currently using two, for a total of 150 feet.
Re/ the OP's question about routing coax out of the cabin, I drilled a hole in my wall and fit a bulkhead connector for 1/2 pvc on the outside, and an A/V passthrough on the inside. This was the neatest option, and it doesn't look too odd. When travelling I seal it with a 1/2" threaded male cap.