I decided to take the $2,000 limit challenge. Here is what I came up with.
Canon T2i w/kit lens: $900
Canon 55-250mm EF-S zoom: $230
Vivitar DF383 Strobe: $130
Protective Filters/Cards/Camera Bag: $300
This leaves you with about $440 to spend. Depending on what your priorities are, some choices:
Decent Tripod: $150
Photoflex umbrella, light stand and flash shoe mount: $150
External Microphone for video (Shoe Mount Boom) and Hood loupe for viewing: $200-$300
Lens upgrades: With your budget, you could switch out the kit lens for the Tamron 17-50 VC f2.8 ($549) or the telephoto for the Tamron 70-300mm VC ($400)
If you are on a budget, don't buy any newly released camera. It's like buying a new car â€“ you will pay a premium for the latest model and on your budget, you can't afford to waste money. Because you want to keep the camera for several years, I debated between the T2i and the 7D. I ultimately decided to recommend the T2i because I just don't think the 7D fits your price range. Lots of complaining here about the 60D, but in my opinion no other manufacturer can touch the 7D or the T2i in their respective price points, so that's why I recommend them.
I was hesitant to recommend a kit lens, but with the $100 price differential between body only and kit lens, and since you don't already own any lenses, it's hard to pass up the kit lens. The 55-250mm zoom is one of the best bargains Canon makes (sure, it's plastic-y) but it is sharp and has IS. I put a premium on sharpness (a soft lens is worthless in my opinion), and am willing to put up with the light weight and plastic given how well the lens performs for its price.
You will soon want an external flash, especially if you want to try portraits. The Vivitar is a dedicated flash, so it uses the Canon TTL exposure system. More importantly though, it has a built in slave, so you can trigger it off camera with your built-in flash.
You will need something to carry this all in and a shoulder bag is your best buy and most flexible option. You'll also want a card with lots of memory and speed and you need some Daylight or UV filters to protect the front elements of your lenses. These aren't optional purchases, but they are easy to forget about when adding up the dollars.
Finally, some choices to make:
Soon you will want a good, solid tripod. Expect to spend at least $100 to $150 (of course you can spend more);
If you are interested in portraits, an umbrella, light stand and mount will enable you to set up the strobe off camera, and trigger it with your built-in flash. This simple set up will yield very nice, flattering portraits and help you learn lighting;
You mentioned video. If you get into video, you will need an external microphone and some type of hood loupe to view your screen. Of course, you can spend tons more on follow-focus, fluid heads for the tripod, etc. etc. but from what I can tell, these two items are pretty much essential (full disclosure, I don't shoot video)
Finally, you may not like my lens choices, and want to switch them out. I've listed a couple alternatives that could work within your budget. I do not own these lenses, so can't vouch for their sharpness or quality. But I am intrigued by the new 70-300mm which Tamron is marketing as "the sharpest ever." Again, I want my lenses sharp, so that interested me.
Finally, read reviews before buying. Not just in the photo press but on-line. Check out the Adorama customer reviews for products you are considering, as well as similar reviews on BestBuy.Com and other sellers' sites. These are from actual users and will give you a better feel than the limited audience that reads this forum.
Now, a word to my fellow forum readers. I hope you'll rise to the challenge and put together your own $2,000 package for this upgrader. If you can do a better job or have constructive recommendations that fit within the confines he or she has provided us, have at it. I'm not particularly interested in reading nitpicking comments from trolls, but if that's your thing, so be it.