Three things that would scare me on a rim: deep rust pitting, particularly if they overlap to form lines where the rim is thin (also a badly rusted retaining groove for the ring), poorly done modifications like the welded on plate shown in the first photo of your post above, rims that are split along the centerline of the rim, (as opposed to at one edge, see Firestone RH-5 rims for the centerline split). If none of those are present, I like your idea of a light cleanup and paint to see what happens at the tyre shop. I am not suggesting use of Bondo or other schemes to hide damage, just making sure the rim looks sound and cosmetically good. Make sure they are a long-established heavy truck tyre shop and not your local car repair joint. The car repair types are rightly cautious to work on things they aren't trained to do and which if improperly done can hurt them. A 2 or 3 piece rim is most dangerous as it is being inflated (and also somewhat if deflated due to blow-out on the road). As a result, they should be inflated in a cage or at very least with chains to prevent the ring from flying if it slips off the rim.
Comment, the rim shown with a 5 stud attachment might be a 10 bolt rim with 5 hole reinforcement plate with studs in alternate holes in the rim (usually on the front axle).
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