Advice for choosing hiking boots that won't hurt my ankle?

You said you’re not worried about the price.

There are lots of places to get custom made boots. Don’t know where you are but a search for your location might find you a local boot maker. There are also many custom boot makers who do online fitting. Many are cowboy boots but there others. Expect $500 and up for custom boots that will last the rest of your life (with repairs, re-soles, etc.).

Just a couple examples; I have not bought from these places but have had my eye on Gokey boots for a long time: