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How hard would it be to paint a 22nd series Custom 8 engine while it's still in the car and make it as good as possible without pulling it out?

It's not hard to do the actual painting. What is hard is doing the prep work. Cleaning, masking and taping is tedious. I use acyrlic enamel if I can't get engine enamel in the correct shade. Any automotive paint store can match the color if you provide a sample.
Just be sure to mask EVERYTHING! Overspray will find any uncovered area. Try using heavy disposable dropcloths and cover the whole vehicle.

You don't have to spray it. I put it on with a brush. Of course, it doesn't look perfect. If you're making a show car, than spray painting me be better, especially for the cylinder head, oil pan and valve cover(s).

If you go that route use plenty of aluminum foil, it is great for forming around hoses and wires, just scrunch it around these things, paint away and then pull it off and discard.
Remember:there is no such thing as overspray, the correct technical term is "undermask".

Yes, with some care it's possible to get a very commendable engine paint job with the engine in the car. As has been pointed out, cleaning the surfaces and masking is the hardest part. I'd remove as many accessories as possible, the generator, starter, distributor, oil filter, hoses, carb linkage, etc. I'd even think about removing the manifolds and then using Eastwood's high temp SS manifold paint on the exhaust manifold - upon heating it will attain the appearance of fresh cast iron. While the generator, starter, distributor are off the car, they can be more easily detailed separately.

Use the spray enamel for the smoothest surfaces like valve covers, oil pan, etc. though if you thin the brush-on enamel a bit, on the rough cast surfaces you likely won't see the brush strokes. Removing the passenger side inner fender will make it much easier to do that side of the engine.

+2 on the aluminum foil! Great tool, cheap and reusable!