I figured rather than just speculate I would put together a few maps to show line-of-sight coverage for the proposed location in Woodbine. This map shows a 30m antenna height line-of-sight to a 1m (roughly man-sized) endpoint. It's not a perfect representation of coverage as it's not accounting for signal diffraction or multipath signal however it's a good indication of where your best signal will be.
When I get a bit more time I will look at what other options might exist.
Additionally, it's worth mentioning that this map DOES account for land cover data such as tree's and buildings, it should be fairly accurate as this is an older community but of course it is subject to discrepancy over time..