I'm often asked about buying a telescope, what would I recommend, usually by someone just getting interested in astronomy. While this may seem like a simple question, there most assuredly is no simple answer.
First, by far the best thing to do would be to join a local astronomy club, and attend an observing event with the club. This is a great way to see a variety of equipment first hand. Second, a lot of people are intrigued by computerized goto telescopes that can find targets for you. My experience has been that these are more challenging to set up and get working than you might think. Often people get frustrated and give up before they even look at anything. They also are more expensive than "find it yourself" alternatives. If you want to start by looking at some planets and the moon, you don't need a goto scope.
Here's a recommendation to a fellow interested in buying a telescope for his father for Christmas with a budget of ~$200. (Note I would recommend you plan to spend much more than this, but...) Many of the points apply to anyone. Below that, see additional links.
I'd recommend establishing a budget and going from there. You also need to consider your father's ability to carry, set up, and use whatever you buy him.
You can get a decent new telescope for around $200. I'd recommend something simple like a ShortTube™ 80mm Refractor (go to Orion and search for "shorttube 80") or similar; sometimes these can be found for $170 new, and they include two EPs (sorry, "Eye Pieces" for those new to astronomy.) This scope would need a tripod, but "any old" camera tripod would do. These have been coming down in price over the years, and you may not be able to find a used one that's cheaper than a new...
If you can't spend at least $150, my opinion is that it will be difficult to buy a new, usable telescope at that price. You might want to consider binoculars.
As far as used scopes, someone already suggested astromart.com, though astromart scopes tend to be mid- to high-end equipment more than budget stuff. This would be more of a place to look for your second or third telescope, not your first usually.
Here are some good links, one to Sky and Telescope's "How to" site, and another to Orion, a vendor with a good selection of budget stuff.
Update: I really like my new Astro-Tech 66mm scope, though it's probably a bit small to recommend as a first telescope: Astronomy Technologies AT66ED Refractor - Dick Locke's Review
Here are several excellent sources of information, explained better than I would be able to ;-)
A Really good (and long) article from scopereviews.com is here
Orion, a good source of info and entry-level astronomy gear
If you're in Houston, stop in at "Land Sea and Sky" to talk to the experts there and see actual equipment.
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