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Filing on-line is easy...
The main things that trips up some are: "word mark"? -for most, the answer is yes. And the "ITU" (Intent to Use) part - if you're actively using the mark(s) now in commerce, then answer no to ITU question.
More fundlementally though, the real difficulty is determing what mark(s) to trademark, in what class(es), descriptions, etc...
If you have some time, lookup other marks, including those in other fields, to get a feel of how to best go about determining what mark(s) to register, class(es), and the optimal description to use.
Be wary of 3rd party TM services, because some don't do much beyond simply file paperwork; that you already can do yourself.
If going the professional route, best to hire a TM attorney who will work with you one on one. Expect to spend several hundred to more likely a thousand or two depending on number of marks and complexity, PLUS registration fees which will be around $700 or so for each registration.
On a related topic, common law trademarks (ie. not registered with the USPTO) are often still quite enforceable, including in UDRP challenges...
The date that typically matters is the first date of active use in commerce not the date of filing (except for ITUs). So don't feel rushed - take your time and do it right.
Ron
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Domagon - Website Management and Domain Name Sales
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