It's all practise and experience. To start with do it how you're comfortable. Once you've had a couple of bad experiences with open vented drain downs chasing air locks about, that's when you realise that many a time a drain down is not the way to go. I remember going to a house on a Sunday morning, not long after I started on my own, trv leaking, had a quick look and it had split the olive, but it was a funny 1/2 olive and rubber o ring. So thought no problem I'll drain it and change the valve. Twenty minutes later I'm filling the system up thinking champion. Four hours later I'm still trying to fill the system up and get all the rads working.