Yes, of course this process can and should be automated.
I do not know existing solutions for it. But it is not a problem to write such program. (You are welcome to hire me
)
How much would you ask for a program like that. What the program should do is create a transaction which has 19 inputs 19 outputs pays 1 satoshi fee than spend the unconfirmed coins from the other wallet (which just got the coins in the last tx) and repeat that x times.
Not entirely sure what you're trying to say here?
( I am not sure that 200 txs will enough to flood the network )
Well 500 tx's must be enough because 3000bytes X 500tx's is approximately 1500000bytes which is 1500kilobytes and that is an overkill.