I had the same behavior. This was introduced with v10.20, when both WiFi and Bluetooth are enabled upon start. Then the Edge will freeze with Checking being displayed. If you disable WiFi, it'll start without freezing. If you have a phone paired, it'll automatically upload your activities and sync via phone connection.
Even after Garmin fixes it, I'm going to let WiFi disabled and will just enable it at home for a quick sync as its giving longer battery life as being enabled for the whole time.
I'm on my fourth 1030 (previous three were all replaced due to the blue halo problem), and all four of them have had the same problem of multiple BT disconnects and then reconnects to the phone during the course of a ride. And I've tried three different phones - same problem with all of them. With the same phones, if I borrow my wife's 1000 and use it, it never loses connection, which points the finger squarely at the 1030 as being the problem.
I haven't enabled WiFi on any of the 1030s.