Mike,
What radio will you be using? Is is a Uniden or Unication? If it is a Unication, there is a chance that you won't need an external antenna. If it is a Uniden, you probably will need one.
One thought is to go with a mobile antenna and a ground plane kit. As far as feedline goes, probably 9913 or LMR 400, minimum, for a run that long. As you know, there is a lot of loss at 800 MHz.
I actually use one of the mobile antennas, on a magnetic mount, on a pizza pan near my Unication. It does improve my signal, but it really isn't necessary for me. With ARMER, on a Unication, I can hear my sub-system and the surrounding sub-systems. I don't need to listen to more than that.
Jim
This Tram Land Mobile Base Ground Plane Kit will convert your NMO mobile antenna into an Omni base station. It comes with 20.5 in. ground plane stainless steel radials and has a 200-Watt power rating and a 100 mph wind load. It is easy to install on any 2 in. pole or pipe.
www.homedepot.com