What is the best tool or set of tools to perform trademark clearance searches of designs and design elements for products/apparel?

The answer is: as soon as possible. Trademarks can take 1-2 years before you go through the entire process. You can apply for a trademark yourself on the USTPO site. Might help to have a lawyer or paralegal help you if you are inexperienced. A simple filing costs a few hundred in fees depending on the nature of the filing. (not legal advice).

Hi: The US Patent and Trademark Office has some great resources, including solid search functionality which lives at: https://www.uspto.gov/trademarks-application-process/search-trademark-database Kerby

Having worked in the domain name industry since 2001, I would always suggest a trademark search before acquiring names. Please keep in mind that when registering a name, you agree to the Uniform Domain-Name Dispute-Resolution Policy (UDRP) as part of your registration contract. This means that you agree not to infringe on rights of others with the registration of your domain. When selling a domain name, it really comes down to your contract/agreement with the buyer. Depending on the details you might be held liable for any potential trademark infringements at a later time. DIsclaimer: I am not a lawyer, it would be best to consult with a lawyer.

Yes. That is the whole purpose of the USPTO filing system. Whoever is first to file gets the mark. There is common law usage which they could argue but first to file is generally upheld.

For clarification. If I understand correctly, this is the womans business and you currently own the logo/word mark? For starters. If you filed the mark yesterday. You still do not own it officially. There is a long process of showing proof of use and paying the government fees. If you were my creative and squatted on the mark, I would take offence. There are other ways to extend your services that you should consider before this tactic. I know that might not directly answer your question. But, she is a non-profit and it might be best way to cut ties off and prospect new clients. On the other hand - if you need a stash of proposals, i used to own a creative agency to send and help you get started.