I have shot a signal quite far using a modified Primstar dish (
http://trevormarshall.com/biquad.htm ). The pringles can will not do the job, its very directional and only really gets about 8 - 10 db. What antenna are you thinking of using? Your going to loose about 4db off the top of whatever they say that antenna will put out. Even more depending on your cable and connections. Not having a line of sight, you need to blast as much signal as possible. I pretty confident I could connect with the conditions you have.
Post a link of the antenna and cables your going to use.
Scott