It's a bit busy but that's loads better. And as for 'something more eye catching than white' there's few shades more eye catching than white. A well chosen tie and white square look excellent. Patterned squares can look great but don't go down that road because of an ill-placed desire to be different, go there when it's most appropriate with the nature of the outfit.
depends on how you wear them and how you care for them. If you regularly clean and buff them the scratches and scuffs will fade and the leather will patinate. If you're constantly kicking them around and abuse them and keep them dirty then any shoe will look like shit. Also the Indy is nowhere near a dress boot. It's 100% casual, wear it as such.
Those are pretty bizarre, they're like a sneaker with a bon welt. They'll work with jeans, don't wear them with anything dressy they will stick out as completely out of place to most everyone, not only nitpickers.