First part, if the address already exists, there’s no need to have it twice, so the display may be confusing, but it’s not a problem. Second part is. I can confirm that when first entry (with address) is disabled, second one is not updated and address disappears from list. It looks like bug.
That domains can be used in address-list was an extra added function. A address can only exist one time in the same list.
WWW looks nice but is in fact an error made in the past to mix a sub-domain with the top domain. So if we choose to use always WWW (redirect) for top webpages then all would be right and your problem would not exist.
You’re focusing on wrong details, those two MikroTik hostnames are just example. They can be any completely different hostnames that just happen to resolve to same address.