Get some tubular box sections and watch yourself get your ass kicked by 15 year olds.

I got my trispoke and a zipp 950 for around 600 bucks.

Honestly though, I think you're over thinking this and just need to get out on the track, figure out what you need THEN spend money. Going in guns a blazing is a waste of money, and especially on the track if you're not fit, you really can't spend your way to victory.

BTW: You are not going to enjoy time trials. No one does.