Companies could also end up thinking, why spend $3 million buying a single generic .com name such as Boston.com when you can spend much less and own an entire extension such as .Boston and have unlimited domains on it.
A lot of people are saying Boston.com looks better but that is because you are familiar with .com for the last 15 years. 15 Years ago people would have probably told you an actual book enyclopedia is better than a website for information because that is what they had always been used to and that websites look weird. Ask someone today which they prefer to use, a book encyclopedia or Wikipedia.org (if book encyclopedias even exist anymore lol). People have been adjusting to changes since the beginning of time and they will continue to do so.