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I had a friend that was real into 2m SSB, he could talk hundreds of miles, far beyond line of site, with less than 100 watts. basically everything I thought I knew about VHF, well I had to rethink it.  I know for 2 meters they made several rigs that are now discontinued, and seems like I recall seeing an old rig from the late 70s with SSB, however I have never seen a SSB rig for 440, only transverters, which I think would be the cheapest way to go for SSB.  Typically they HF rig on 10 meters with transverter to get to 2m and 70cm.   A re purposed CB might work nicely to drive the transverter also.