Actually I believe RS232 is defined as a protocol used to transmit digital data over an analog medium. While the voltage level is reasonably important, it's actually defined in a fairly broad to leave a lot of room for noise and errors (or lack thereof). I'm pretty sure the actual range is +- 15v on the transmitter side and +- 25v on the receiver side.
A lot of different devices use different voltage levels for the actual transmitting and receiving leading to the occasional incompatibility or glitch between them even though they are both within "spec." Ever have a laptop not communicate with desktop over a serial line even though all the settings are the same on either end? Generally it's the voltage levels that are causing the grief and there isn't much you can do about it.
The actual transmission is defined as a start bit, some amount of data bits, a parity bit if needed/wanted and some number of stop bits. To actually transmit, both sides have to agree on a all this stuff as well as a speed; otherwise, strange and generally undefined things happen. The speed of the transmission is probably irrelevant to this application because of the low amount of data needed.
Damn, I'm a nerd!

This is all from a fairly hazy memory from my long-ago EE days so please correct me if I've goofed anywhere. Anyway, most of this is irrelevant to the discussion so I'll just leave it at that.
If all you want is a simple circuit that will transmit a signal to drop a line low for an instant (to trigger the timer), I could probably whip one up fairly easily and cheaply. I was just trying to be clear on what you were asking for and my engineer side wanted to over-complicate the situation as usual.
While the 1 mile range might be a problem, there are a couple of ways around that without building/using a high-powered transmitter. Would it be sufficient to have a shorter wireless range but be able to add to it with a cable? If you had a few hundred feet of cable on either end of the transmit and receive side, you could seriously extend the range using low-powered wireless stuff. Stuff being a technical term!

Seriously, it would help solve the range problem and keep the hard and heavy stuff (like a car battery) away from the timing lights.
Another possible wired solution if the current wires are just to short would be to use a signal conditioner or something to extend the range of the current equipment. Also, if you wanted to use the RS232 approach but stay wired for greater reliability, I believe the range on RS232 can approach 3000ft if used with a low baud rate (in the 2400 range). With 2 transmitter/receivers in series, you could easily cover a mile.
I'm sure we could come up with couple of other options depending on what you're really after. Let me know if you want me to further pursue any of this and I'd be happy to.
Jim