First of all, welcome to Audioholics!
I have been pretty frustrated because unlike with headphones there are no good guides (that I have been able to find) that say like: at this price range here are some good recommendations and here are the pros and cons that you can use to narrow down the search based on your use case.
There's a good reason for the lack of simple guides to speaker shopping. Speakers really do vary widely in their sound and in their price. The cabinets alone can easily be the most expensive part of speakers. They aren't just cosmetic, the cabinet design and construction qualities play a distinct role in speaker sound quality. And I haven't mentioned the important role that a room plays in the overall sound of speakers. These aren't issues with headphone design.
Compared to electronic components, such as disc players, receivers, pre-amps, or amplifiers, speakers come with a much wider variety of performances and sound qualities. As a result, money spent well on speakers will go much farther in producing good overall sound quality than for any other audio component. Because there is such a variety of speaker styles and designs, it's not surprising that there is also a large variety of personal tastes among speaker buyers.
To directly answer your question, yes, it's time to start listening to a variety of different speakers in your price range. Bring your own music with you as you go listen. Other people can tell you what they prefer, but it works better if you learn what you yourself like or don't like. Just one hint, most people (myself included) like the sound of speakers with a frequency response that is as wide as possible and measures as flat as possible. As long as you keep with that, understand that spending more money can get you deeper bass response and speakers that sound "more detailed" without unpleasant sounding exaggerations or noise.
The price range you have chosen includes some truly excellent bookshelf speakers. Many people start out in price ranges lower than that, and I usually keep my silence. But I can name three bookshelf speakers, all roughly $900 per pair that in my opinion are as good sounding as anything else sold. They are all sold internet direct, and you will not find them in stores. But because they are built and sold directly by excellent speaker designers, you will get far more performance for your money than if you bought speakers sold by audio stores.
Salk SongSurround – Even though these are marketed as rear channel speakers for a surround sound system, these make excellent monitor speakers. They come in a variety of excellent veneer finishes.
Philharmonic Audio Philharmonitor – these are probably the best bang for the buck. Although they are temporarily not available, they might be worth waiting for.
Ascend Acoustics Sierra-1 – These are similar looking and similar sounding (but not identical) to the Salk SongSurrounds. I'm more familiar with the above two speakers than these, but they are still an excellent option.
