1) There seem to be two things that impact the number of rounds necessary, your description and how many names are taken in that area. With the same description, usually one or two rounds is sufficient to see how well you're going to do (sometimes you'll get a bad batch of workers, but one or two rounds is usually enough to smooth the variance). However, if you're changing little things it might go longer. For example, if I was to do more rounds, I'd probably add something to the DebtEye description to ask for more "safe sounding" words, and less sort of sleazy words (e.g., "ez" or "instant").

2) $5 is below cost, our twin goals for the moment are to gather more data about what sorts of names we can do well on and to get our name out there. We'll probably do a survey or something later of real buyers to see what the actual price should be. There's also some raw-ness to the results right now (e.g., you'll get 2 or 3 good results with 47 bad results) so we're keeping the price relatively low until we have better automated filtering.

3) Unfortunately, when we were just starting out we didn't have Domain Refinery (and a naive implementation doesn't work terribly well for reasons I won't go into). As a result, we did the days of brainstorming followed by purchasing an overpriced name route. However, we've since used Domain Refinery for our naming, and in fact, Domain Refinery is named using itself. The top three names for what is now the Domain Refinery were domainrefinery.com, nolongernameless.com, and brainstormdomains.com. Ultimately, we liked domainrefinery.com best because it signaled the refinement aspect that we wanted to contrast against competitors.

(I'm one of the co-founders.)