Koboi,
Don't feel alone. I've been running a production co' for almost nine years and recently made the jump to HD. For two years, I watched the trends and evaluated cameras and held onto the purse strings with a 'death grip' until I found something we could work with.
So, with that in mind ask yourself these questions;
What do I want to do with the footage? (meaning, what will be the ultimate distribution method.) You mentioned some potential projects, but not how anyone is going to see the final product. Fortunately, there are viable options for an 'insurgent filmmaker' like yourself (too underfunded to be 'independent' but better educated and skilled to be considered 'guerilla'.) Your distribution points these days are the web, DVD and mobile content. Just as an aside, broadcast TV is a potential point, but very difficult to break into.
What video format do I want to use? (i.e. standard definition DV or high-definition HDV) Again, go back to the first question to help you decide. At the moment there are some good single-chip cameras that get some dang fine imagery for around the money you're looking to spend. Problem is; they're going to be consumer-grade rigs and you will have to be very familiar with the camera's limitations and idiosyncracies in order to make your work look professional and not like some nimrod on YouTube. Added to that is what recording format would you prefer? With a small consumer 'crashcam' I absolutely prefer tape. If anything goes south, at least I've got the footage. I hate that consumer rigs are now mostly harddrive based. If the harddrive goes before you can download your shoot... (insert loud fart-like noise to simulate footage disappearing into nothingness.) Many consumer cams also have the option of solid-state recording via flashcards which by the way is awesome because it cuts your 'capture time' down to how long it takes to download it. Drawback with that is, flashcards at the moment are expensive and many cameras are proprietary (meaning they want you to only use their company's cards SONY!!!!!! PANASONIC!!!) which also gets expensive. If you can find one still, get a hybrid (tape/flashcard) unit which is great because tape is mad cheap and you can pick-up more flashcards as you can afford them.
Last and most important, what type of computer and editing software do I plan on using with my camera? Very, very important detail to consider. Unless you plan on just being a shooter and just 'handing off' your footage to an editor (good luck with that,) you're going to have to purchase those things. Good news is, if you're shooting straight DV (meaning standard def DV) as long as you have a firewire output on your camera and one on your computer just about any software capable of non-linear editing will work with it (do your research first!) On the otherhand, HDV has gained excellent ground and most well-known NLE software can handle it (Premiere, Avid, Final Cut, Vegas, blah, blah, blah ad nauseum.) Be advised; you'll have to deal with deciding on what Operating System Platform (Windows, Macintosh, Linux, etc.) you want to work with and how much all that is going to cost you. To get a better idea of that, read the other discussions on the virtues/disparities concerning PC's and Mac's.
Though I said that the above was the last, technically it is so this is an 'oh by the way'; Support gear is very important (i.e. batteries, tripods, camera bags, etc.) You want to pick a camera that is compatible with as much support equipment possible to help you put together a professional kit. Just because you have a consumer grade camera doesn't mean you want to show up to a shoot looking like a tourist. Les Stroud of the 'Survivor Man' series until recently used nothing but consumer grade cameras to produce his show, but he still had a professional kit. I've done many a shoot using a 'crashcam' and always enjoyed watching client's faces change from incredulous to 'okay he knows what he's doing' when I whipped out a decent tripod, lens adapters, specialty filters and so on. Of course, you're not going to have all of that up front and neither did I. You'll build up your kit and when you're ready, you'll find yourself 'champing at the bit' to move onto a more professional rig. Then you can start the whole process all over again! Joy!