I'll admit the optics aren't good, but it's not like she waited a month to tell everyone after the fact that she had pneumonia. There's really no big conspiracy when it comes to the Clintons. I think they, especially Hillary herself, are pretty introverted and private people that have trouble with being totally transparent about all aspects of their lives (yes, Bill is extroverted, but I think he still values privacy). I think Hillary is a very proud person and tries her best not to display any weakness. Trust me, everyone knows someone like that.
Pneumonia is highly contagious, yet she chose to go out and take part in a highly public festival on the 15th anniversary of 9/11, in NYC of all places. That was deeply irresponsible. Then, being the deceptive person she is, her campaign said that she was "overheated," which makes no sense since NYC today was a lovely 80 degrees. I was out all day, and nobody fainted from "overheating." After retreating at her daughter's $10M penthouse apartment (bought for by clinton foundation donor money, most likely), she released a note from her doctor which stated that she was diagnosed with Pneumonia back on Friday.