if you like what you see you have flexibility to act on it. If you don't find anything you like, sounds like you're happy with your home so there's nothing lost there.
I couldn't continually move after x amount of years (as your boss mentioned). moving can be a pain in the ass and there's costs associated with that too (time and money). however, if you're looking to land in a good school district and you've already come up on some money from your initial investment it's as good a time as any to shop around.