What would you do with it?
Old homemade well
I would hang some windchimes from the bars and then place baskets of flowers all over the top. This would be a great place to decorate seasonally! Perhaps you can paint the bars with some paint made for metal. Black would look nice. You could plant hostas all the way around it as well.
I would hang a really cool watering Can if u have one , or I would find one in a thrift store. I would also agree that the handle should be painted.
You could hang a watering can from the top bar or hang a planter with plants like petunias or calibrachoa that will cascade down. I wouldn't paint the bars at all, I like the look as they are and you'll have a maintenance issue. If you're worried about damage from rust, cover them with clear matte spray paint by Rustoleum to protect them from further damage. Since you're in FL you could plant some perennials around the base of the well to add some interest. If you like succulents they would be a good choice and not need a lot of care. Also you could plant some other kind of flowering plant or liriope (mondo grass) that wouldn't spread out of control or require a lot of maintenance. As you probably noticed, I'm into things that don't require a lot of upkeep! I want it to look nice without requiring a ton of babysitting.
Those options would work in KY too! You'd have to select succulents that are cold hardy though. I'm in upstate SC, zone 7, so I have succulents that are cold hardy to 20 degrees which covers most of our winters here. The mondo grass will die back in winter, mine does, but will pop back up in spring without missing a beat - they're tough.
What about the concrete part below? What would you do with that?
I’m in Greenville.
You could paint the base with spray paint for a fresh look. Or build around it with wood fence posts.