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anything to stabilize that end is better than nothing! but looks like it should work. a spring loaded caster will just allow for some still though. i don't see a spring loaded in your drawing just the pics you posted earlier but still.
No spring . A spring would not be a bit better than the pivot all by itself. The caster,if that is what you decide upon, needs to be positive height adjustment(threaded shaft if you feel adjustment is desirable) with no give.