First off, your chance of crashing will be 7x less than on the MD-11, so that is nice.
I believe the MD-11 is newer, so I think the automation will work better than on the 744. The VNAV on the 744 is "high maintenance". If ATC does not mess with your profile at all, it will work. The more speed and altitude restrictions and/or vectors you get, the worse it does. It takes a long time to process changes, and is liable to stop working all together. It is not so nice to hear in the the sim when the highly experienced instructor tells you he is not sure if the vnav will start the descent at the next point or not, and be ready to manually intervene.
Also, depending on the software load, the database can be quite limited. It is an old processor and old hard drive, so it definitely has its limits!
The plane flies great. I like having 4 engines over water/mountains/desert.
The cockpit, from the capt/fo seat is VERY cramped! It's a 707 cockpit jammed into the top of the 744 fuselage.
Overall, it is very nice. The 747-8, should fix all these automation problems and be phenomenal.
I have only talked to MD-11 guys on the road about their aircraft. If everything else is equal, I would go for the 744.
Also, there are more contract jobs available on the 744 than the MD-11. And, in the US, the 744 and 747-8 are the same type rating, so that is good for jobs.
cliff
KGRB