Rusted rims

I'm almost thinking you might scratch up the filler with your tire iron putting the tire on...filler isn't very hard at all.
I'd try to grind or sand the lip of the rim the best you can and go from there.
Or just use tubes.
 
A good slather of bead sealer on there might be enough to seal them. It’s made specifically to seal leaking beads with rusty and pits.

I used to use Napa brand bead sealer on my 4 wheelers back in the day. Not because of pitting but because I’d blow the tires off the beads jumping and sliding. Solved all my problems and was definitely a strong seal because I’d have to take them to my buddy’s shop to use his tire machine to break the beads.
 
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