It depends on what your area of interest is.
Portraits, landscape, nature, industrial, product shots?
How much post processing do you plan, prefer, or expect to be doing?
How much control do you want? Do you prefer to work with a higher dynamic range in terms of exposure?
You should weigh these factors out.
Do you already own alot of film equipment? Is some of that equipment compatible with a dSLR or digital in general?
Are you prepared to shell out some bucks for digital equipment?
Do you use a basic PC or laptop, or a visual workstation? Mac or PC?
You should keep in mind that if you own a consumer grade PC that you may very well have to sink some cash into it if you want to be efficient in your workflow.
You should have a minimum 1GB of RAM, plenty of disc space, at least a mid-range consumer grade display card (Nvidia or ATI) with at least 128MB of onboard memory.
You'll also need software. Depending on how much power and control you want/need there are some decent and inexpensive(some free) applications.
But if you are/will be doing professional level shoots, you'll want a pro app like Photoshop.
With that in mind, you'll want a monitor calibration system. Not to mention a good monitor.
Once you start to accumulate alot of images you'll want a good backup system. A fast firewire or USB external hard drive is what I'd recommend.
Not too expensive, and you can stack them when you need to add more space.
You can also connect them to an existing LAN so the contents are available over ethernet.
Gigabit ethernet is what I use and recommend. If you plan to move large images around the network quickly, 10-100Mb ethernet isn't practical.
With that in mind, you'll want an asset management application like Lightroom or Aperture if your an Apple user.
Cheaper ones exist but I'm just using these as an example.
You should come up with more specific questions. Or just tell us what the majority of your work will involve.
Anyone here could most likely offer advice then.
For me, post processing is a major part of my work. When I shoot, I shoot with post processing in mind. So film wouldn't fit into my workflow seamlessly.
I also started with digital. Never owned a film SLR in my life.
I come from a graphic design background though too.