Sorry, this may be a long response
race4aliving,
Just like audio you need to find out what types of applications you would be using the scope for; just visual, astrophotography or both. Also, will you just be interested in planetary, lunar and double stars or strickly deep sky like nebula, galaxies and other faint fussies. Each type of scope has its own specialties. Most refractors are better on planets and double stars. Some apochramatic scopes are also good on the larger / brighter galaxies and nebulas but are extremely expensive. Reflectors can bring in much more light due to their sizes and are better on the fainter stuff - cheaper per inch of optics compared to refractors. Cassegrains and Maksutov's (combination of both refractor and reflector) does both but you also have to realize the larger the optics the longer the cool down time (temperature equalization - glass is a funky substance).
I don't know how much of astronomy you know so I will start out basic by saying if you haven't done much observing yet get a really decent pair of binoculars and start using them. My other suggestion would be to find a local astronomy club and use their several different style of scopes to see which ones you prefer. Just like audio, you have the different types of camps: refractor, reflector and the combination of both (also known as a Maksutov or Cassegrain style). The other factor you need to find out about is your local light pollution. If it is a lot of light pollution you might need to go down the refractor road.
There is an online resale site (like audiogon) called astromart. You can get a sense for size, type and dollar amount. Also, two good magazines are Astronomy and Sky and Telescope.
I'm going to assume with your listed budget you already have a somewhat idea of what you are doing and is a decent budget. Some brands for refractors are Televue, Takahashi, Astro-physics (not a chance - they have a 5 year wait list, they also sell for more used than they do new due to the wait list), TMB, TEC (Telescope Engineering Corp), Orion, APM, Meade, Megrez, Williams Optics, Celestron and so forth.
Reflector brands (usually called dobs which is short for dobsonian which is the most popular style of reflector) Starmaster (best is with mirrors made by guy by the name of Zambuto), Obsession, Questar, JMI, Parks, Meade, Celestron, Coulter, Orion and so forth.
Don't forget you will need accesories like barlow lenses, eyepieces, filters and the geek list goes on and on.
Some scopes do not come with mounts so you may need to look into that also. You have Alt Azimuth (pan and scan) and equatoral (can be gear to track objects so you don't have to keep readjusting the scope to keep the object centered. You also have GOTO in this style in which the mount will find and track objects automatically for you).
Some good websites are: Orion, Company7.com, scopereviews.com, starrynight.com, astromart, astronomics.com.
I hope this helps and I hope I didn't ramble on like mulester7.
Bryguy