For arrows and such, you might try using the graphic fonts like monotype sorts, webdings and wingdings...
And like the map effect, you can wipe-on a hand drawn arrow graphic that has an alpha channel.
You can also create frames and circles using the gradient generator, by making the inside of the circle/square transparent and outside transparent too.
You can keyframe size and position for any of the above.
HTH, MPH
Addendum: (re your last post) If you create your graphics as 655x480 PNG files, they will look great.
Check out Camtasia. It has a function that allows you to use a 'pen' (much like when they draw on video on the fly on sports programs) while recording the screen. you could record a blank window and draw. then overlay the recording on your real video. that's the only way I know of to really get a realtime drawing effect where you have the freedom to actually draw and create the animation (short of buying one of those drawing-over-video devices).
Here's a non-vegas answer to this question: NewTek (the Lightwave/Video Toaster people) are giving away free copies of AuraDV (A DV only version of Aura 1) to those people who go to a participating local NewTek reseller and see a demo of a lightwave product. AuraDV is esentially a video paint and compositing program. It can't even touch Vegas Video on the compositing side, but it makes for a handy video paint application in one's video toolbox.
okay, I'm responding to my own post. I tried using Camtasia for creating the drawing effect, and it works great.
the way I did it, is I turned on the recorder and placed the recording frame on a black area. (I used the Vegas preview window since it was convenient).
then I enabled the ScreenDraw function in camtasia and drew some pictures. you can draw freehand, elipses, arrows (works great), boxes, and even a highlighter which is translucent for emphasizing portions of text. you can change colors but use white at first. you can also change the width of the line.. so you can do monday night football style with a fat line, or use one-pixel wide lines.
so the recording I end up with is an animated drawing sequence in AVI format, white pen on black background. just drop that AVI file on the top track of your project and change the compositing mode to SCREEN. now the animated drawing will play on top of the video and the black background becomes transparent. you can pan/crop/split to fit whatever it is you are trying to draw on top of.
I was also able to draw on a still shot easily and ONCE I got it to draw on moving video, but for some reason I couldn't get that to work again. might have something to do with my buggy ATI card but I don't know.
a big bonus... you can download Camtasia and use it for 30 days FREE. that's plenty of time to do some drawings.