After taking a peek through some of the telescopes at a star party, people are often inspired to try the hobby for themselves, but need some guidance on where to start. Namely, what kind of telescope is a reasonable one with which to start? Lately, I've been seeing two different opinions on this.
The classic one is the same one I see in many hobbies: Get the cheapest one you can that does just the basics, so if you decide it's too much trouble, you're not out too much money. The typical recommendation for a telescope of this type is a Dobsonian. This type of telescope is named after the type of mount it has which was invented by John Dobson. In this case, the mount is what helps keep the telescope so inexpensive: It's an Alt-Az mount which means it simply moves the telescope up-down, left-right.
In many cases this is perfectly adequate. However, since the Earth isn't flat, that means that you can't easily track an object in the sky as it drifts out of the field of view. With other types of mounts, the base will be tilted to compensate for the Earth's curvature, so you'll only have to move it in the left-right direction, but with Alt-Az mounts, you'll have to move it right and up. After a little practice, this shouldn't be a problem, but if you've ever used the other type of mount (an Equitorial), you'll grumble at such things. Some Alt-Az mounts have computers connected to powered drives to keep the telescope aligned or find objects for you (known as GoTo), but I can't say I've seen such things on a Dobsonian. It's usually on smaller telescopes, and Dobs get big fast (which is one of the cool things about 'em!). Although not connected to drives to move the scope, I have seen some with the computer that figures out where objects are and can tell you which way to move to find it. So there's some assistance out there.
Another problem many have with Dobsonians is that they have a very long tube. This can make transportation difficult for people with smaller cars. I know recent designs by some companies (Celestron at the very least), have begun making "open tube" designs which allow the assembly with the secondary mirror and eyepiece slide down some rails to make transport easier.
What to take away from this is that Dobsonians are great telescopes, but they require more hands-on work than many of the other telescopes; you will be moving the telescope yourself to find objects and to keep the telescope aligned once you have. Unless you have an accessory to tell you where to move, you'll also have to learn your way around the sky significantly better than many other modern scopes, which can be a good thing. But it can also be a very steep learning curve and turn people off from the hobby altogether.
Which is where the second train of thought comes in: To help people dive in and be able to start spotting galaxies right away, another way to go is to get a smaller telescope, but one that has more advanced features. This, in many ways, makes the hobby far more approachable.
There's many good choices of telescope for this as well. Small 4" scopes start in the range of about $500. For comparison, for around the same price, you could get a Dobsonian telescope with an 8" mirror. Since light collecting power is related to the square of the radius this would mean four times as much light being collected for the same price.
But what does that difference mean in the experience? It's really a difference in what sorts of things you'll be able to see. Regardless of what type of telescope you have, you'll need one that's at least 8" to start seeing "deep sky" objects, which includes most galaxies nebulae, and other such things. With smaller telescopes, you will be limited to brighter objects like the moon, planets and bright double stars. Not that there's anything wrong with this. For most amateurs, who live under light polluted skies, the bright city lights will wash out many fainter objects anyway. Thus, for many practical purposes, both will work just fine. It's really when you have opportunities to get out to a dark sky location that these difference will start jumping out at you.
So to wrap things up, I think there's several important factors to consider:
Your location - Do you live under light polluted skies? If so, then bigger won't necessarily help you so much and you may want to go for some bells and whistles.
Your free time and dedication - Do you have ample time to learn the sky? It's a steep learning curve and can be exceptionally frustrating. This is especially true if you live in a light polluted area and there's not enough stars by which to get your bearings.
Your budget - The real limiting factor. If you had all the budget in the world, then buy out the Hubble and get to it.