It will likely go ok. The biggest pain is the clean up. The common things that can go wrong are that the pulley doesn't pull off the crankshaft or that you find that it had been running with the sump bolts loose and the mating surfaces get hard to seal.

Hopefully, you'll only do this once, so I would use some Permatex 2 sealer on both sides of the gasket.

Also, when you go to reinstall the sump, try to make sure that the cam stays mated to the crankshaft gear, and that you have the marks in the correct position.
sometimes, the "boss" that the end of the cam gear fits into will be sloppy, and will let the cam be disengaged from its correct position, in relation to timing, when you reinstall the sump. A length of sewing thread will hold it in place until you get the sump back on the block. BT.DT.
I have used a product called "Indian Head Shellac" for that job. Just a light coating, to hold the gasket in place. And--do use a new gasket!!