I am in the same situation as you (sorta). I am currently a student and have been in your position, say about 5 or 6 years ago. I must say that I have come a long way since then. I have learned SO MUCH by being on television sets as well as working on my own projects. I can tell you right now with 100% confidence that you do not need a single light or piece of grip equipment. I made probably 20 good and bad short films since my first project. I never used a single light or piece of grip gear for those films. Granted, they may not have looked great, but I gained all of the production knowledge I have now. My latest film used a small light and grip kit (1Ks and 650s). I was only able to properly use that because of my previous knowledge of how to do everything else right.
As for you, I think that you should take your XH or your flip video or whatever you have and shoot a film this weekend. You don't need boom mics, paper work, lights, flags or any of that junk. Mount the mic on the camera, throw it on a tripod and go. You need to just know what its like to be behind the camera, direct actors, set up shots, and more importantly, develop a good story. I think that your first film should focus only on story, as well as portraying that story via the camera. Even if the lighting is terrible, shoot it, look at it in post and find out what you can do next time to achieve the lighting you need. Remember, if you don't have a story, you don't have a film. I only say all of this because your experience seems limited (I noted that you did not know what 24p was).
WHEN it comes time for lighting and grip, you should just rent it all. A Matthews C-Stand (If you don't know what a C-Stand is, then you are definitely not ready for them) costs about $175. If you need 10 of them, thats $1750, one third of your "Budget." They rent for $3/day/weekend at most rental houses. If you have a 3 day weekend shoot with 10 stands, thats $30, plus you don't have to store them when they aren't in use. Rent rent rent.
Last thing. Use your friend's Final cut xpress. its almost the same thing as FCP without multicam and crap you don't need yet anyways.