I painted mine a few weeks ago, by just masking off around the D-Ring and only painting with the enamel. It looks great and was super easy. If it ends up getting scratched up, I could just paint them again.
Don't forget the sales tax hit you will get by buying 2 cars. I would factor in the sales tax on the bronco sport towards the markup on the Bronco. I think on a Big Bend, if you're patient enough you could find a 5k-8K markup.
I also have this issue, I think the short 1st gear just makes it tough to get the timing right putting it into 2nd. I've began just starting in 2nd gear in most situations with no issue.