Well that's a big jump going from a point and shoot to a DSLR.
Even in price for a entry level DLSR and a High zoom lens for it.

You can get a Pentax KX with the stock 18-55mm lens and a 55-300mm lens on Amazon.com for about $674.

Maybe someone could say if the Olympus E-PL1 could fulfill your needs.

Yea I guess I shouldn't complain about cost I've probably spent $900 on three different cameras in the last two years and haven't been happy with any of them.
It just seams like a big jump going to a DSLR. I may be wrong but it just seams to me you would have to know a lot more about cameras and setting to jump to an SLR camera.

SLRs do have auto mode to get you started. I see the Nikon D3100 has a "guide mode" for novice's. Canon I know has excellent website for learning photography as well.

To stick with P&S I'd also look at Casio lineup, esp FH100.