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I'm building a commercial product, so .org isn't a good fit here. And .net to my understanding has been greatly abused and doesn't relate to anything specific at all. It might be not that bad for a hobby but in my case the product targets enterprise users.

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As you said that you are targeting enterprise users, I would suggest to negotiate with the owner of .com domain. Have you contacted them?

The domain has been registered 5 years back, so I don't have any hope to get it cheap. Besides, I'm still going through idea validation and as such don't want to spend any additional money on the project that might not fly or will change direction

You realize .org can be used by for-profit organizations, right? In my opinion it's the one that users find least surprising after .com.

I've had a few clients go with .org or .net . My impression is that the general public is "aware" of .org -- there's enough of it in use -- although they may not immediately remember that your site uses it instead of .com . I think .net is more unusual and so perhaps confusing, for the general public.

I do wonder whether your registering a variant means that the desired .com domain will remain renewed/tied up, gambling that you -- or a competitor -- will want to acquire it.

HN-centric example: Patio11's appointmentreminder.org

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