Adam, you will get many opinions on this topic - i bet the reason not many responses have been posted to your thread is because this issue (gears) is slaughtered on a daily basis.
i will say that i dont know that i would be racing my only car - one that needs to commute me 90 miles somewhat frequently.
that said, the shift points: i have a mildly modded stang, and have to fly through gears anyhow - were i to have gears, i would be shifting non-stop. some guys love this - it is not my cup o' tea.
when dragging, if you are keeping stock-ish wheels and
suspension (i assume you want to run it in the quarter - unless i missed it, you did not say what kind of racing you wish to do), you will have traction issues as it is. stick gears in there and you will spin more.
then when you are near the end of the track: guys with stockish cars and stockish gears (3.5:1 and under) seem to often be able to hold 3rd as they finish.
were they to have a steeper gear, they would possibly spin more and have to shift once more during the run.
do note that im making huge generalities, but the point was (as i said in the first post) that you might want to do some homework before deciding. if i had a 300 dollar car, i might be taking it real easy on it, myself.
Michael Yount (aka Guru) has posted a link to a site with some calculators (i know there are many sites with this stuff, but i liked his). if you search for posts by him on gear threads, you should get an idea of what you might want to do (or find a bud with a similar set up and get his input).
good luck.