Be extremely cautious while communicating with the owner. Even if you casually agree to buy the domain via email, the communication might be used against you in court as a legally-binding contract should you change your mind. Until you’re absolutely certain that you want to make a deal, agree to buy the domain provided that all the terms are agreeable. This will leave you an escape hatch if things go south. 

A short, one-word name (ex. cat.com), and especially .com domains, will be pricy because simple titles have a lot of potential uses, meaning people probably already check them out on their own. If you are going after a registered .com domain, you will have to contact the current owner, and even then, prices could be high for misspellings and multiple word domains. In the past years, companies and individuals have settled for bizarre names, misspellings, and old tricks like adding “the” or “my” to the front; note, however, that this will also reduce domain performance.
Make sure you can use their SMTP servers for outgoing email. Many hosting and domain name registration providers will not let you use their SMTP servers for sending emails. They assume you can send email via your internet server provider’s SMTP servers. However, a great many ISPs and broadband providers will only let you use their SMTP servers on their branded email accounts (i.e. [email protected]). This means that if you use your own email address (i.e. [email protected]), you won’t be able to send email via their SMTP servers. There are workarounds but you shouldn’t have to go to the trouble.
Even if the term isn’t trademarked, don’t buy domains that are just a variation of another domain name. This means avoiding plurals if the singular is taken (mediatemple.net vs. mediatemples.net), hyphenating a phrase (media-temple.net), or adding “my” or some other preposition (mymediatemple.net). Alternately, you might consider buying these variations yourself and set them up so that if someone types one of the variations, they are redirected to your main site.
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