You're mixing up two different concepts: (1) trademark rights and (2) cybersquatting and infringement.
[Yes, I know the domain names that you've provided are just examples. The following analyses would be the same if they were the actual names.]
Trademark rights: Can you develop trademark rights in buyme.org? Maybe. Trademark rights develop only by using a word, phrase, logo, color, sound, whathaveyou, in commerce to brand a product or service. Registration of those rights is a good idea but not required. The potential mark must, however, be capable of distinguishing the product or service from all other identical or related products or services. A trademark attorney will have to evaluate whether your domain name is capable of doing so. Many business and product names are either generic for, or merely describe, the business or product and so cannot serve as a trademark. Moreoever, if another has already begun to use that mark, or one confusingly similar, to brand a product or service then the second comer cannot, generally, develop trademark rights in that same mark to brand that same or a related product or service. That second comer would be an infringer of the rights developed by the first.
You have not used buyme.org in commerce and so, even if it's capable of serving as a mark, you have no trademark rights in that domain name. BTW: Use of a word or phrase as a domain name does NOT, by itself, create trademark rights in that word or phrase. It must also be used on the website itself as a brand identifier -- that is, as the name for the business or as a tag line.
Cybersquatting and infringement: Would you be cybersquatting or infringing if you publish an auction website at buyme.org in light of already-existing buymenow.org and buymi.com websites? Maybe. The answer depends on whether the owners of those sites have trademark rights in those domain names and, if they do, whether your publication of a website at buyme.org would likely cause consumer confusion in the marketplace and whether it was bad faith on your part to publish that website.
Only your own trademark attorney can walk you through these issues as applied to the real domain names and websites at issue. Good luck.
The above response is general information ONLY and is not legal advice, does not form an attorney-client relationship, and should NOT be relied upon to take or refrain from taking any action. I am not your attorney. You should seek the advice of competent counsel before taking any action related to your inquiry.
Attorney Ballard, once again, offered a really generous response to your question.
I agree that we need to be clear on the issues, but yours is a fact intensive scenario and the only way for you to get helpful actionable legal advice is to consult a lawyer in private and have a non-hypothetical analysis done. I would first want to make sure that we are talking about a protectable mark to begin with and not a generic or highly descriptive domain name.
Whenever you endeavor into investing in a trademark it is very important that you conduct the proper clearance due diligence upfront and before you submit an application to the USPTO. In the US, this means searching under both federal (USPTO) as well as common law because trademark rights stem from use in this country NOT registration. This means that acquiring a federal registration does not necessarily mean that you are not infringing on another's intellectual property. See the link below for a detailed explanation of the due diligence process.
I suggest that you consult with a lawyer in private and discuss your objectives in more detail. You can start by calling around to several for a free phone consultation, get some insights then pick the best fit to work with.
DISCLAIMER: this is not intended to be specific legal advice and should not be relied upon as such. No attorney-client relationship is formed with the law firm of Natoli-Lapin, LLC on the basis of this posting.
Your situation is not particularly unique. Lots of domain names have zero activity. Others are incredibly active and commercial. Amazon.com and eBay.com are two of the busiest commercial sites in the world.
So let's run through your examples, to see how this works:
1. You have emails dating back to 3 years before a competing site launched where you propose launching a site by the same name. Too bad for you. It is use, not proposed use, that confers trademark rights. Your emails mean little legally.
2. Now there is a site by a very similar name [buymenow.com vs buyme.org in your example] that is a landing page. They get now trademark or servicemark rights for a landing page. There needs to use "in commerce" and since no commerce, no trademark or servicemark rights are established.
3. You find a "beta" site with a phonetically identical domain name [ buymi vs. buyme] that is making commercial use, although in beta. Test marketing is commercial use, so buymi would have priority over you. However, the geographical area of use might be different and the product or services might be different. Actual facts are needed to come to an actual decision, but potentially you are blocked by that one.
4. You pose a hypothetical that is not actually your situation and ask us to tell you if your situation is legal. Well, what I think about that situation is that animal is a "Hellifino", a beast that is produced by failure to state actual facts. You have to get to an actual attorney with actual facts to get actual actionable advice. Otherwise, the Hellifinos take over.
5. Unstated question - "what should I do". My advice is forget this conflicted mark and pick something unique. Given your town, perhaps "Hacienda Hutch" or "Hacivendor". Get something that generates protection rather than conflict.
I am not your lawyer and you are not my client. Free advice here is without recourse and any reliance thereupon is at your sole risk. This is done without compensation as a free public service. I am licensed in IL, MO, TX and I am a Reg. Pat. Atty. so advice in any other jurisdiction is strictly general advice and should be confirmed with an attorney licensed in that jurisdiction.
Trademark rights arise from use in commerce, not registration. The mere fact that you purchase a domain name is meaningless from a trademark law perspective. The issue is whether you have been using it in commerce to operate a business, If not, you are probably out of luck. If so, you may have an argument that you are the senior user---notwithstanding these other registrations. One thing is clear---you need to retain IP counsel to evaluate all the facts and circumstances. It would be a big mistake for you to use this web-site as a substitute for retaining legal counsel----if you make a mistake, one of these other trademark registrants will sue you, and you will face enormous legal fees and problems.