well i'm going to put in my .02 cents worth, 3 questions
1. will you read All the instruction manual, i'm not talking about skimming or the quickstart. i'm talking about maybe only 1 chapter a day, with the camera in your lap, changing the settings and dials as you go, until many of the settings and creative results become instinctive
2. will you read any basic book about photography, doesn't have to be brand new,or even recent go to the public library and take one out, but not a highly technical book such as ansel adams zone system, too complex for right now, you want to get some basic knowledge of exposure and lighting
3. will you buy or borrow a book about digital photography, this one should be only a couple of years old,
if the honest answer is yes to all 3, then go right to an entry level dslr with a kit lens, you are only talking a couple hundred dollars more or maybe less than an advanced point & shoot, even consider if budget allows a good quality lens, something along the lines of 17-55. 18-85, these are just sort of a reference framework, buy a used entry level body from keh, go out and learn all you can, if you follow htese steps you'll know when your ready, when the camera is holding you back creatively, and by that i mean when you can upgrade the body and achieve the same results with less thought process and less menu/setting tweaking, go with 1 of the big two, canon or nikon, easy to find good deals on used bodies, known company with a committment to the current mount/lens lines, go with whichever body feels right in your hands, go try out similar size bodies on for feel at best buy/circuit city, etc, the big box store doesn't need to know you are just sampling
now experiment away with your gear, see what happens with different settings, don't chimp and delete, upload them all to the pc, review on the monitor, then delete, if it doesn't please you, try to figure out why, is it technical, is it aesthetic?
now it's time to go back to the library, now it's time to look at others work, if outdoor work is your thing, then it's time to look at galen rowell, john shaw, people, anne leibovitz, street pj, cartier bresson, weegee, manray
learn from the masters, wonder why they stood where they stood,see how they framed things
sorry for the length, but i honestly feel this is the path to walk towards better photography, i'm still on my journey, probably will be all my days