Check with
http://www.3starinc.com/ for Rohn towers. They offer commercial grade self supporting and guyed options. Then there are also consumer grade 'push-up' types to consider.
Cable loss varies with frequency. Presuming RG-6/U coax, the VHF signals on real CH-8 & CH-10 & 13 can be pushed 500' by the PA-18 preamp. UHF channels would only make it about 250' before needing to add another amplifier. If you have very long runs of cable, we can help you figure out how to get the signal from the antenna to the TV(s).