Take a look at Telescopes 101.
A lot of good information there. 2 things to remember…
You get what you pay for.
More aperture is better.
The problem here is, while a Dobsonian will give you the most aperture for your dollar, it’s not really suitable for terrestrial observation.
A nice, portable Maksutovwould do nicely.
This has a flipdown mirror, and a straight-through viewing port on the back, so you can put anerecting prism on the back for [del]spying on the neighbors[/del] looking at birds and ships.
I have a Meade ETX 125 that is similar, and love it for quick looks around the sky if I think of something, and a couple of larger scopes if I’m in the mood to drive out to a dark sky area for a few hours.
Please stay away from the Newtonian reflectors you see at Best Scam, or similar stores.
They are cheap, Chinese-made, entry level toys and not worth your time or money.
While smaller scopes can suffice for beginners, they often disappoint in their optics, magnification, and imaging, making you not want to use it anymore. Craigslist is full of them.
I personally think an 8 inch scope is a minimum for actually finding and enjoying deep-sky objects, but that’s just me. I have larger and smaller scopes, for different purposes.
Quartz is spot on with his suggestion. Your local astronomy club members will be happy to have you out to the country to view differing scopes and setups, and guide you to purchasing the best scope for you and your needs.