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@hugo are you using Omni directional antennas?
Ten years ago, my local radio club (Santa Cruz mountains did a neighborhood survey of simplex propagation using different antennas and wavelengths.
The South skyline club (Woodside, Portola Valley) did a similar survey on their side of the hill. Their results surprised us!
We got better results on 2m and they got better results on 70cm.
The difference was enough to make some stations unreachable depending on wavelength.
The hills facing the ocean had deeper peaks and valleys while the Bay side are more regular and smooth.
We gave them our diy J-pole tuned perfectly for something like 462.550MHz and they got spectacular results.
So consider the shape of the land if you need to optimize.
73