I discovered that getting somewhat of an actual feel for these two sites worked better for me when I took a more general approach to this assignment, hence, here are some of my first impressions. I liked the format of Craigslist much better from an organizational standpoint. One can readily find their main search categories as they are all conveniently listed on a single page. I had no trouble finding a successful starting point for a search, no matter what I was looking for. Boston.com, on the other hand, was a bit confusing and not nearly so straight forward. I found myself often rather guessing in which section I should start. Once I located a general category for my search, however, I discovered that both sites had their stronger and weaker points as far as a further breakdown into subcategories was concerned. For example, within the personal ad category, Craigslist offers more subcategories of specific types of relationships, but as far as searching for concerts in the Boston area is concerned you will find it much easier to specify your search by music genre in Boston.com. Both sites offer keyword searching, but an added feature which Boston.com includes, at least in some of their listings, is that of tags which are extremely useful when keywords don't get the job done.
As far as the variety of listings is concerned, I would give the edge to Craigslist but that may be due, in part, to the fact that one can get a pretty clear idea of all that they have to offer via a quick scan of their homepage- not so, with respect to Boston.com. The latter however, provides more in depth coverage of topics within each category. Aside from listings, articles on appropriate subjects and other types of pertinent information are also included as useful supplements.