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Hello and thank you for your question. I will be very pleased to assist you. I'm a practising lawyer in England with over 10 years experience.
May I clarify for the avoidance of any doubt (though I have very little) this is not a situation where you were booked on a flight and then cancelled due to delay and rebooked and paid again for a second flight which was also delayed? I believe I am correct to understand from what you say that you held a ticket to fly on the original plane and that was delayed twice and eventually you flew but still under your original booking and payment?
Thank you. The compensation provisions relate to a your ticketed to contract as opposed to the actual aircraft involved. In other words your rights to compensation derive from your contract (ticket) with the airline for each leg of the flight. So in this case you have a right to compensation on the way out and way back (providing in the latter case it is an EU regulated airline).
From what you say you had a thoroughly miserable experience involving two cancellations. However because the second flight was still provided under the original booking (i.e. it was not a new booking you had made after cancelling the first) it does not give rise to a second head of compensation as you hoped. Your compensation for this delay would be calculated by comparing the time you were supposed to originally arrive with the time you actually arrived. The situation would be the same even were you to have suffered several more cancellations on this leg I fear.
The only way I am aware you can claim more than once for effectively the same trip is to cancel the original booking obtaining a refund and then making a new booking which is also cancelled by the airline.
I fear thererfore in these circumstances you are likely to be limited to one claim for compensation though this should be for themaximum amount of 600 Euros. You should however also be able to claim for two nights of accomodation if it was required and/or transportation costs, and food and drink vouchers for both days.
I am very sorry this is unlikely to be the information you were hoping for and I do hope you ultimately had a good trip. Does the above answer all your questions or is there anything I can clarify or help you with any further?
A pleasure - If I can assist any further as the situation develops please do not hesitate to revert to me