In what circumstances should you configure multiple DHCP servers on the same subnet?
You want more than crappy uptime.
My understanding of using more than one DHCP server is that your clients will use the
nearest DHCP which could be unpredictable.
This is probably why DHCP in Windows has the ability to work in a failover scenario with synchronized access? You can couple 2 servers (more exactl: address areas) and have them synchronize between two servers, which nicely means you have none of the issues you seem to have ;)
but I don't see what the advantages of doing this.
Uptime. Maybe in your world hardware never fails, in mine it does. Pretty crappy when the only DHCP server fails, especialyl with IPv4 where machienes will not pick up a IP when the server goes back online. HAve fun getting everyone to restart his machine in a larger company. Note that with IPv6 that changes as machines get dynamic notifications when the assigned networks change.