Video for videojongs

I apologize if this is covered in a thread somewhere. Feel free to direct me.

I need a basic understanding of this whole process.

I've been running some "coach the coach" programs for one of my town's youth sports programs. Instead of doing this live each year, I was thinking of creating a series of how-to videos, then posting them on the website. I used to do a fair amount of photography but I have a limited background in video (I can certainly do better than digitaldeath's latest effort, but that's not saying much.) I've contacted the local HS video class teacher and he's willing to hook me up with a student for $20/hr--unfortunately I don't have that kind of budget. He's told me to expect 4-5 hrs of total time per 5 min of finished video. I'm also stupid enough to think I can borrow/rent some video equipment and tripod, etc., go Uncle Rico and pull this off.

So, in layman's terms what's involved in producing ~15, 5 min videos?

I have both Mac's and PC's. A 2005 era Sony HD handheld video camera and a $200-$300 budget.

Thanks.