You can lose a trademark case if you have been too selective in who you complain about. Especially if you are seen to be ignoring small time infringers but only going after those with big pockets, the case can be thrown out.
Lawyers tend to err on the side of sending C+D letters to anyone, such as the case of Sun and the island of Java tourist authority. The apple/orchards bit was irony - it's in the dictionary.
The other problem is judges/juries and computers. The trademark has to be in the same field, but the courts aren't always as tech savvy as HN readers and frequently regard all 'computer stuff' as the same field. So while we would see a CRM package and a forum website as completely different as a magnolia plant shop and a magnolia paint company - a judge might not.