I've been to WDW at least once, often twice, a year since my first trips a kid in 1986. I've had a few years with 3 trips, and I lived in Orlando for my first year of college at UCF. I'd guess I have 45-50 trips total? My family members are all Disney people, my parents first joined DVC in 1994 when I was in college and my siblings still in lower school grades as Christmas break was the only common vacation and having points made it more affordable (back then it was $55/point!) to go that time of year. Now my husband and kids enjoy it too. However, as of last year, we have started cutting back to once a year, as we have other places we want to go and other experiences we want to enjoy as a family.
As for runDisney events, I have done Princess weekend (the Glass Slipper Challenge plus the 5k in 2 of 3 years) times in 2014, 2015 and 2016. I did Avengers Infinity Challenge + 5k in 2015 so I could get my Coast to Coast medal. My husband and kids joined me for that 5k and it was so fun doing it as a family. I just attended my first Marathon weekend last weekend. I did the 10k and full. I honestly thought it would be one and done for me, as it is really tough schedule wise for our family. But, I had so much fun I am sure I will do it again. I do want to do Dopey someday, maybe 2020? I never would have started running regularly if it hadn't been for runDisney, so it seems fitting I can't seem to drag myself away. As both a wine fan and a Star Wars fan, I'd like to do those two weekends, but with our new 1 Disney trip a year policy it may take a while to get to them all. Unlike some I really enjoyed running in Anaheim as well for Avengers, so I do hope rD brings those races back.