Amplification is fairly easy to engineer. RG-6 coax has 6 dB or less loss per 100'. 2-way splitters should be given a loss budget of 4 dB, 4-way splitters 8 dB and 8-way splitters 12 dB. Take a look at these examples of using the NM value on your TVFR:
http://forum.tvfool.com/showthread.php?t=109
If the antennas you've used to test with were UHF only designs, as many small antennas are, you've not necessarily proven as much as you may think you have. What make and model antennas have you tested with?
As I look at the path profile for the two ABC options,
http://www.tvfool.com/?option=com_wr...ALLTV%26n%3d12 &
http://www.tvfool.com/?option=com_wr...ALLTV%26n%3d14, I have to be honest, both present rather steep obstructing terrain fairly close to your location. While my personal choice would be to whole-heartedly 'go for it', I know I would be taking some risk. My enthusiasm to 'go-for-it' would be less if I was forced to aim through trees.