To be constructive...
I don't think the "auto-pinger" is such a good idea. While I agree that it would nice to not have to think about it...I think in practical use...It's just not feasible.
For one...If you insert any dynamics or time-based processor and perform a ping without it being bypassed, you will most likely have issues with sync. I always bypass my hardware before I perform a ping, and when playback works (ie. no [Buffering] or glitch-ness) it is always in sync (even with parallel compression). This might work okay with hardware EQ's...But I tend to not risk it. Bypass, ping, forget about it.
My system runs at the same sample rate and same buffer size always. Even though I have three different AD/DA boxes, the sync settings are consistent for each box. Therefore I have ReaInsert presets for using each hardware output. This works great as I don't have to mess around with anything when I want to use my hardware.
I just wish ReaInsert wouldn't cause Reaper to lose it's mind.