Hi,
@0daymaster having the same issue, I did a quick & dirty implementation of multiple ping targets for 2.4.4-p3. I can give you the patches if you want. However there is dpinger to pach/recompile aside to support multiple targets, which can be quite tedious if you're not familiar with freebsd and if you need to cross-compile (for arm in my case). With the patch, dpinger will ping each host as often as it was before and will report an average on all hosts. So, if you set 4 hosts, it will generate 4x more pings in the same time, and if one host is down, it will report 25% packet loss.
As a side note, it has been a surprise to see that dpinger is using threads with shared variables without any kind of thread synchronisation. If there is any issue there (and I think there is), using X hosts will multiply by X the likelihood to trigger it.