Well I ran a two server event and it went very well. The points system was based on time so it was worth racing in server 2.
From our league...
Qualifying & Points.
On the Saturday before the race, all entered racers go into a live Ventrilo draw at 8pm and they are randomly assigned a server (via live draw) where they will both qualify and race.  Qualification takes place in that server for a place on the grid on the same server.  No racer needs to switch servers at any point.
All racer's final times are recorded on all servers and their actual overall position decided by their time.
The points system is based on the Nascar system (the 5, 4, 3 spread) which is as follows:
Position    Points
1st    185
2nd    170
3rd    165
4th    160
5th    155
6th    150
7th    146
8th    142
9th    138
10th    134
11th    130
12th    127
13th    124
14th    121
15th    118
16th    115
17th    112
18th    109
19th    106
20th    103
21st    100
22nd    97
23rd    94
24th    91
25th    88
26th    85
27th    82
28th    79
29th    76
30th    73
31st    70
32nd    67
33rd    64
34th    61
35th    58
36th    55
37th    52
38th    49
39th    46
40th    43
41st    40
42nd    37
43rd    34
DNF's score behind the last finisher of both servers and how many laps completed against other DNF'ers.
The draw will be exciting and you'll be anxious to know the result of the other races before you can start celebrating...
Even if there's a multi-car pile up or you crash and you're not racing for position on your actual server, you still cannot take it easy, because you're also racing the clock, as you don't know what's happening in the other server.
Live Server Lottery Draw
Join us on Ventrilo at 8pm (UK) to hear the live draw for the server sorting. We will post and email the results following the draw. This draw will decide which server you qualify and race in and most importantly, who you are racing. This Ventrilo server will also be available during the races.
For those that don't know how to join Ventrilo:
Get this: 
http://www.sanandreasmodernmod.net/VentriloMix.zip, then install.
Open program, choose Ventrilo 2.3. Then join server 85.214.103.242, port 3784. Join channel Sonicrealms and start talking.
BTW, you need sound on your computer and a mic if you want to talk.
I will perform the draw by having a Server 1 & Server 2 group. I will then pick numbers from a lottery type machine based on their confirmed racer number and they will go into the alternative group, all live via Ventrilo.
The draw will also be on IRC.
Edit: You could probably use [SR] Darktimes LFS points to work out all this for you, so should be easy enough - 
http://www.lfsforum.net/showthread.php?t=31513