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Assuming you have the motor off the boat I would say the transom in the day while outside in the nice sun, and work on the motor in your garage at night.
Transom first, motor second. If you fix the motor first, you will be tempted to put it in/on, go out and run it. When you do that with a bad transom...you can lose your engine, and worse.
I have to disagree with the first two poster... You fix the motor first. There is very few instances where a hull transom cant be fixed, there are plenty of reasons a motor cant be fixed... You are way better off having a good working motor and looking for a good hull (hulls are cheaper) than having a good hull and be looking for a good working motor (look at the prices of working motors). The price of fixing a motor might be enough to stop a project... Seen it plenty of times here... Good luck in whatever you choose.
I have to disagree with the first two poster... You fix the motor first. There is very few instances where a hull transom cant be fixed, there are plenty of reasons a motor cant be fixed... You are way better off having a good working motor and looking for a good hull (hulls are cheaper) than having a good hull and be looking for a good working motor (look at the prices of working motors). The price of fixing a motor might be enough to stop a project... Seen it plenty of times here... Good luck in whatever you choose.