Sadly, it doesn’t seem possible to see the live segments until you are within the prescribed distance, so you have no way to really predict what you will see in the moment. Sucks because I’ve done some hunting with starred stuff, only to have to ride it “blind” and go from memory on the start/stop, which is not great unless you really know or dissect the segment before hand.
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I had similar problems which were solved by a software update, you can always create a segment on your doorstep for testing. Also downhill segments won’t sync.
https://support.strava.com/hc/en-us/community/posts/360035410392-Strava-Live-only-works-for-flat-uphill-sections-
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Just what I was about to post!
I don’t remember for certain, but I think I solved this by un-authorising and then re-authorising my Strava account through the app. Then they appeared.
(You might need to wait a little bit for your Strava routes to re-sync as well)
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That did it! You are the man!
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Thank you for calling Wahoo customer support. 
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I need to leave well enough alone. Based on the good feedback above (and my few instances of oddities), I decided to unlink and relink Strava and my Elemnt app.
Now I can’t get it to reconnect with a “Username or password incorrect” message. ARGH!
Per a google result, I tried changing my Strava password, with no better results on connection to the Elemnt app.
EDIT: the last tip in the thread above was the key. Unistall Strava from the phone. Open Elemnt app, authorize (which triggers login info, since Strava app is now gone), and all is back as needed.
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