Well, some thoughts about dSLR´s I think they are worth mentioning:
1-You´ll most probably have to upgrade your computing set up. In my experience, nobody has talked about this, but it is a very important factor. You won´t be taking jpeg´s any longer [else there isn´t THAT much sense in buying a dSLR for shooting jpeg´s as you´ll loose quite some editing power]. File sizes will increase dramatically from your point and shoot if you choose to shoot RAW. Handling them -not just storing them- can be a little bit of a nightmare.
2-Starting to understand a dSLR vs. a P&Shoot.
The speed factor is very important [as a behavioural aspect]. A DSLR has a very different speed of use compared to other cameras, as you won´t use live-view as much -or shouldn´t, depending on what you´ll be shooting-. Meaning that your own ergonomics are very important in that subject. How the camera handles, if the lens is easy to change -regardless it is a zoom or a prime-,
You are on a tight budget [though, 1100us $ for a get-go system is not exactly cheap or low. 500 US $ will be a "tight" budget, and still buy you a 10mp dSLR]. As for that, you will want to go for legacy lenses as much as you want [were they zooms or primes]. For that, there are only two brands that stand out:
Sony and Pentax. Sony still has the possibility of using Minolta lenses [or KM lenses], with both metering, aperture and autofocusing capabilities. An A700 could be a very good deal to start with, as prices will have come down -and it is a very good camera-.
As for Pentax, their bodies can take up to M42 lenses [those via an adapter], but still will give focus confirmation on them and have an easy metering with the green mode and button. And there are gazillions of old lenses [the range is the A, A*, A Special, F, F*, FA, FA*, FA Limited] that will allow the camera to do the metering with no problems, plus all the weird and cheap lenses with the K mount [adopted mainly by french and russian companies]. That alone will allow you to experiment with primes that, otherwise, are extremely expensive [such as the Helios 44 85 1.4, or the Jupiter 9 series, or the Petri and Chinon series].
In my opinion, the very best advice has been given: go to the store and try the systems. But bring along a card of yours, and review the results YOURSELF at home.