Rich, i got into dslr just about a year ago now and cannot believe the difference it makes over a point and shoot.
There are others here at PCA who are way more advanced than me, but this is my input.
I entered the dslr world with a Nikon d40, ive since bought different lenses for different types of photographer but tend to stick with my birding lens Sigma 120-400mm os apo.
Your budget is not going to allow you into dslr or the the top end telephoto compacts...well not a new camera.
I would suggest to you if a used model to go for the Nikon P90 or as a cheap startup option the Nikon Coolpix 5700, one here in budget on Ebay click here
We could write endless recommendations, the sky is the limit really.
I would never go back to a point and shoot as my main camera...but thats just me.
Im still learning and enjoying it evry day that goes by.
If interested what a beginner can do with a dslr, have a look at my photostream over at Flickr click here though i would warn you that lenses are what makes this so special and come at a cost...
If you would like any more advice , i am more than willing to try and help.