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For long cable runs, you will definitely need a pre-amp. RG6 will lose up to about 6 dB for every 100 feet of cable. Without a pre-amp, a lot of the hard-earned signal coming from your antenna will be lost to the cable.
If you're talking about going up 100 feet into a tree, it sounds like you may end up with even longer cable runs (~200 feet?). If the cable lengths start to become excessive (several hundred feet), then the situation can be complicated by the need to daisy chain amps (not recommended if you can avoid it).
Hopefully, adding a pre-amp to your existing setup will be enough. You should end up a few dB better than where you're at now, and that might be enough.
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