Phil - My amateur mechanic quick marine diesel checks

If it takes a long time to start like 30 seconds+ cranking somethings not good. Check its compression with a gauge. Check the CSV fuel filter to see if the fuel is clean. After it starts check its cooling water is exiting the engine. You can also check its sea water intake filter if it has a clear top to check that cooling water is coming in. Listen to it and slowly increase and decrease revs and check for out of place clanks, whirring or vibrations. ie worn bearings, shot valves. Run it hard in gear against the mooring for a bit or out on the water. Check no black smoke from exhaust. A little is OK flat out. Do the same astern to check gear box. Feel the gear box temperature. They often have their own cooling system. Once the engine is hot try stopping and starting it again. A classic is that diesels start when cold but not when hot. You also want to check that the engines stop mechanism works. While its running check under the engine for drips of oil or water, a sign of seals or gaskets shot.
Then leave it idling in gear a long time and feel if the block is too hot. You can check with a temperature gauge. Then crank it up and leave it running at cruising revs and also check if its block is hot. Make sure the cooling water exiting the boat isn't mixed with steam or oil!