Same here, LiveTrack is very buggy even with firmware 8.11 beta on my 1030. My 530 with the latest FW is buggy as well.
Now that 9.0 is released give this a try and update your comments. Make sure your cell phone has good data connection, live track relies on it. Also the Garmin Connect Mobile app must be loaded on the phone for connected features to work (iPhone at least).
buddy of mine has the same issue with his 1030 Every ride i track him at some point the signal is lost and never reconnects. His girlfriend at home says when she looks to see where he is, she gets the same "no signal. trying to reconnect" but it never reconnects. You find a solution?