Missed the start of this during a crazy Monday, so here's a couple answers.
August 1: Do you prefer to use real dice, a dice application or program, or use a diceless system?
I prefer to roll real dice, at a table, but these days playing online via Hangouts and/or Roll20 is so much more achievable on a regular basis, so in terms of simple volume of rolls, recent data indicate "virtual dice" (I happily pay a monthly subscription to Roll20 to support their service, and it's worth every penny.)
August 2: What is the best game session you have had since August 2015?
This one: https://youtu.be/mz7f6RFBdKQ
My favorite line is right around 2 hours, 27 minutes, when Mike sighs, closes his eyes, and says "I really hate this place. I hate this place so bad," about the creepy cabin.
I really need to run more *World games. It just suits my GMing style right down to the ground; it's like running Amber Diceless, but with dice, in a weird way.