Hi,
1) What was the very first item you purchased and the year it was purchased?
My first purchased item was Camera Shutter, when I’ve been editing Bongiorno Massimo Showreel in 2015.
2) What was the most recent item you purchased?
My recent purchased item from @arnabkumar.
3) Tie-breaker: What’s been your favorite Envato highlight over the past 10 years?
Since I am only 1 year active here, I could say only for last 12 month. I have enjoyed participation in Most Wanted: Sports Music. I guess my recent highlight was publishing SoundCloud and Facebook arcticels and gaining “Wordsmith” badge 
Then featuring in Envato Famous 5 is always great!