Click not firing underlying object - INCONSISTENTLY

Here is a pattern. I am working on a pretty large project to basically change my tests for a BIG UI change within our AUT. I work on the test project happily day after day. I get a couple of great runs in the green. I go to run it again over night while I am merrily sleeping. I come in to find the CLICK behavior is not working. Click not working is a bit mind bending, right? Of course click works. I try to run again while looking at an example test, and it works fine. Take a look at the (sorry large) MHT for System Smoke Tests / AddCommentCodeSmoke. In the log folder Step: Add and Check, a click is occuring. I can see evidence in the log that the click is occuring. The error occurs then on the next action because the expected screen is not there. My autowait timeout is set to 20000. So there should be plenty of time to load the page for the next event as it searches for that object. 

This is happening in many tests. I am trying to imagine if increasing my piddly (100) delay between events would help? 

Anyone seen t