I second MattyP's comments on aperture... I bought my first scope only a few months ago... an 8" Dobsonian, and already im itching to move up to a 12". Considering you have a nice (and i assume DARK) place to view from, an 8" dob would be a great (and cheap) starting point.. Dobsonians, as was mentioned earlier, are a very simple, non-motorized telescope system with which you will need to have some knowledge of where the object you wish to view is.. The upside however is that you can see a hell of a lot more in an 8" than you can in a 5"..
With a budget limit of $1k in mind, I would be looking at a 10" Dobsonian, these can be purchased for around the $550 - $600 mark.. and will give great planetary views, and similarly good views of brighter galaxies and nebulas.
To this, you could add Digital Setting Circles (DSC). These are (in the most basic terms) an electronic system that will tell you where your scope is pointing, and more importantly, where you need to move it to in order to view the object of your choice..
Photography : Astrophotography is
Expensive. You wont find many people taking pictures of galaxies or nebulae with less than $2k worth of gear (not including cameras in most cases). I and a few other members of these forums have taken images of Jupiter, Saturn and the moon using dobsonian telescopes. It can be done, but it is a fairly frustrating task without a motorized mount.
There are a few sayings that get used a fair bit when new members are contemplating their first scopes...
1. Aperture Rules. Buy the biggest scope that you can afford
2. The best scope for you is the one you will use. Dont buy something too big and bulky/difficult to set up, this will only be a deturance to getting out and using the telescope.
3. Aperture Rules!!!!
You may want to contact an astronomical society near you, and attend an observation night... That way you will be able to have a look at a few different scopes, and get more of an idea of whats right for you...
Hope I've helped somewhat.
Alex.