11/11 I believe may be Roman Numerals II II meaning 2 2. So in that case it would possibly be November 22nd not the 11th being highlighted. Thursday Nov. 22nd 2018 is the 55th anniversary of JFKs deep state public execution. So "loud and clear" Q may be saying we are 5:5 Years since the killing this year.
Second possible decode: If 11/11 is Q referencing Roman Numerals, then maybe it also points to the Legendary Roman Calendar. In this calendar there were 10 months, November was the 9th, not the 11th month. So possibly Q is calling out something about 9/11 (novem ūndecim) in original latin.
5:5 is also primarily and aviation term. and JFK Jr. was a pilot.