Here is a website where you can enter two points to see the path between them. It also allows you to make adjustments for elevation of the antenna.
https://www.scadacore.com/tools/rf-path/rf-line-of-sight/
In my experience, the RF path for GMRS isn't purely line of sight. I have generally been able to get over or around small hills successfully, but not bigger hills.
Your success in reaching the other side of town will largely depend upon how big the "dip" is on the other side of the high spot. If it dips down to 350 feet, you'll probably be fine, but if it dips back to 130 feet as it does on your side, probably not.
