There are a couple of free elevation tools on the internet. I don’t like the conclusions, but I guess it’s better to know.
FreeMapTools has an Elevation Finder tool. With it, one can easily check specific elevations anywhere you click on the map. There is also that less intuitive but better suited Hey What’s That website. I did profiles of my path to repeater with both Elevation Finder and HeyWhatsThat. They seem to agree that my 885-ish foot home elevation is no match for the 1000+ peaks between me and the 949 foot repeater antenna.
Note that the highest elevations are within 3 to 5 miles of home.
The only good news is the orange highlighted area, particularly the skyward piece. This is the calculated propagation of a 145MHz signal between these two points. The fact that I can hear the repeater fairly well is also promising.
At this point, more gain may not make nearly as much difference as more altitude.
The calculated altitude needed for a completely unobscured point to point view would be 170 feet above ground on my end, so lets hope it doesn’t take that much.