They're both very colloquial - as you probably guessed…
dole out the beatings, not receive them
Bearing in mind he's some kind of supposedly-retired tough guy, visiting his old boss, if I recall correctly, his 'job' would normally be to damage people for a living. To dole out is 'to give', rather informally, to usually more than one recipient. It has a hint of 'giving by the rich to the poor'. It's also used in the UK as an informal name for Social Security/Welfare payments, 'the dole', implying a meagre hand-out to all who need it.
The beatings, I presume, is rather more obvious - something more than a punch in the nose.
So overall, he's surprised at the apparent bruising John Wick has. He would always expect the other guy to have the bruises.
dip so much as a pinky back into this pond
This one is simpler.
It's a slightly mixed metaphor though, so I'll break it down...
A 'pinky' would normally just be a colloquial term for your littlest finger.
To 'dip your toe in the pool/pond' would be to 'test out the water' putting the smallest part in to see if it's not too hot or cold.
Another colloquial term for toe would be 'piggy' [from the nursery rhyme, This little piggy went to market…]
So much as is a fairly standard, though probably archaic, term. It could be replaced by 'as much as' or 'even as much as' but not by 'so much like'. Think of it as being more 'the smallest amount possible, or even less'.
In this context it means 'don't do it at all, not even one toe/finger'
So he's just mixing the two metaphors pinky/pond rather than piggy/toe/pond.
He's implying that if John was even to think about returning to his old life, it may just drag him back into that life more than he would wish.
He's using 'reach out' & 'depths' at the end to reinforce the water analogy, implying there may be metaphorical crocodiles or sharks in the water/his old job.
Best Answer
Actually the "to be out" phrase can be used in many ways. It depends on a context. I hope a dictionary (https://idioms.thefreedictionary.com/be+out) and a repeat of the scene will help you.