I’m Canadian, and I had to look on the map to see where Swan River, Manitoba is! I also used the SOTA mapping project to find your closest peaks, which appear to be in the USA nearly 500 km away.
I’m impressed with your desire to take radio to the hills.
You asked about trans-matches. I must admit that even though I have a unit, I never use it, preferring instead to use resonant antennas. The inverted-V when trimmed to length doesn’t need a trans-match, handles higher power with no problem, and works consistently in a variety of locations. If you want to use multiple bands, a couple of links in the wire harness give it to you.
Good luck in your SOTA ventures, and if you venture west to Alberta, please contact me and come and meet the local SOTA folk.