We had a leak in a small portion of our roof. Got an estimate from one place which was high - we chose to go with a friends son who cost less ($250). We did not sign a contract. He just gave us an estimate. He repaired the roof. After the first rain it leaked again. We called him out and he fixed the roof again. This time we painted and repaired the ceiling.
After the next rain - it leaked again redamaging the ceiling. We called - he said he would be out. He never showed when he said he would. Never returned calls. We finally reached him by phone and he said he had been busy. We told him to forget it - his repairs were faulty.
We had the first company come out - $650 (we signed a contract). They said nail hole was not sealed, shingles were not replaced, and flashing was improper which we have in writing. We paid an additional $650 and by the time they came out another rain caused even more damage to the ceiling.
We at least want to get our $250 back from the first guy + $150 we were quoted to repair the ceiling.
What are our chances in small claims court?

Actually not to bad, Even a verbal agreement is somewhat binding in court. When and if you go the biggest asset is if you have your phone records to prove that he was called and given the chance to make it right. That proves that he had a reasonable amount of time to either address the situation or to give a refund.
I'm a contractor and I feel if the roof leaked in the repaired area than then that souls have held. If it was another area that's different. Roof repair can be a pain. I cover this problem by the contract only applies to the repaired area and not others that may pop up. If our patch did not hold we either make it right or return a FULL refund and say sorry.

Signed 21 Boat

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Will you win in small claims court? Most likely. You have the second contractors statement that the repair was poorly done.

But winning is only half the battle. You then have to collect. Unless you know where this kid banks, the likelihood of your collecting is pretty small.

The success of your claim will depend on part on two elements which have not been thoroughly detailed in your post.

1. How wide in scope was the work of the first contractor supposed to be? Specifically, should it have caught any and all causes of the leak and involve the repair of same.

2. Were the deficiencies found by the second contractor (ie. Nail hole was not sealed, shingles were not replaced, and flashing was improper) the result of the previous contractor's failings or were they pre-existing and thus the cause of the leak in the first place?