That happens to me all the time (yes, I´m getting tired of it too) but after something like 10 tries switching between different USB ports and turning AP on/off a couple of times it usually works...
Time to get a new watch maybe, but apart from the above I like my FR305.
It might be worth calling Garmin when you are home. I have found them really helpful on the phone.
And I would love to be there for that run.