[Fitbit or jawbone?]

I have the Fitbit Surge and truly love it @ Susie I have wireless earbuds as well and have not problem listing to my own music. Fitbit is just a tracker really has nothing to with not being able to listen to your music. I either listen to my own or Pandora and I use a couple other apps and still am able to listen to my music.

[Days off?]

I ride my bike on the days off I just started last week and now on week 2 day 1 which I done this morning.

[Heart Rate Monitor ?]

I use Polar chest strap and never had a problem with it.

[Running Shoes]

I just bought the same sneakers going to start Monday.