I have a thought on that...
I used Canon point shoots pretty much from the first model, (advantix film 1998-99 :lol
I also have enjoyed a Nikon D100 from a pawn shop. I've had the DSLR for almost 5 years, they mistakenly sold me $2000 lens attached to the front of it worth FAR more than the camera. I picked up a lens or two to supplement it since then.
Here's my 2 cents:
A DSLR is a huge commitment. Only get one if you also plan to spend at least equal to or four times what you spent on the camera. I was lucky to get a high end lens with my camera. However I couldnt use it in a lot of situations coz I'd literally have to walk 30 feet back to snap a pic with 3 people in it. I supplemented with a 50mm primary lens, and its nice, but still doesn't have the field of view of my point and click. Also plan on carrying camera bags with you everywhere, lenses are bulky and heavy. DSLRs are romantic, but require lots of time, money, hassle, and effort. You'll also Need to get things like CCD cleaning kits, an air dust blaster and may want haze filters for the lenses. If you are interested in a telephoto picture, prepare to PAY, big time. There's no point in having removable lenses and then cheap out on them.
If your interested in a travel camera, I highly, highly highly recommend the other branch of camera you haven't mentioned. I recommend a super zoom model. You know the ones that look vaguely like DSLRs but operate like a point and shoot. My brother got one because we were going on a two week safari in Kenya. Let me tell you, I was incredibly jealous of the speed and magnitude of the zoom.
I think it could be summarized this way: dslr : the focus is on the camera you actually bring extra luggage for the camera and your only goal is to take pictures, period. big zoom: the focus is on the trip, great pictures, enjoy travel as well as take pictures, more ready for all occasions.
For DSLR go with Nikon, don't buy the newest model, get one a year or two old, DSLR has incredible longevity. Save money on the camera body and spend it on a better lens or there's no point in having DSLR. Expect it to last 10+ years service and consider it your new hobby.
For big zoom, I recommend checking out Nikon, Sony, but don't forget Canon. For these I recommend going to a robust camera store with lots of demo models and trying them out yourself. Check out the UIs, speed of lenses, drive speed, image stabilization on a zoomed in video, clarity of photos etc, read camera blog reviews.
Also consider history, Nikon and canon came from camera and lens manufacture, Sony comes from electronics and video recording. They are all good and maturing now, but their histories are still evident as subtle strengths in their cameras.
I guess that was more like 3 cents.
P.s.
No matter what your big camera of choice is, your tiny pocket camera is still valuable.
Don't forget its the photographer that takes good pictures, not the camera or its price tag.
---------- Post added at 06:40 AM ---------- Previous post was at 06:16 AM ----------
I just reread your op and saw your last camera was film?
don't forget to look at the Nikon, canon, and Sony pocket cameras. They are awesome. For your money you can buy a great one! For choosing I recommend the same process as big zoom mentioned above. Pocket cameras and big zoom are better for video recording. Don't be fooled by digital zoom, its crap. All that matters is the lensatic zoom is the one that counts. Good luck!
---------- Post added at 06:51 AM ---------- Previous post was at 06:40 AM ----------
Oh and get a camera that can take HDR sets automatically!!