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Wow, that’s not great. You have my condolences and I hope you manage to convince your city to put some money into a frontage road or path of some sort. I’ve seen some pretty nice rail trails and the like in very small communities, but they take a lot of work and time.
I hike with a FT60 too; it’s simple and robust. It’ll handle San Bruno mountain except for right along the top ridgeline. Walking 20 meters downhill will let it work again. That mountain is just a crazy bubble of RF.
I use two techniques to figure out if the handheld I’m carrying will work. First, if the S meter reads at S9 but the squelch isn’t opening, then it’s overloaded. The second is to call into a clearly viable and local repeater. Failing to open the repeater is a pretty good sign of overload.