Should I grease the drive shaft bearing for a more connected feel or oil it for a faster feel on a reel that will be used for mostly flipping and pitching?

depends on which bearing it is. Some Daiwa reels have three bearings on the crank. One at the base, one on the outside, and the anti-reverse bearing. 

Never grease the anti-reverse bearing.

Any other frame bearings can use either oil or grease.

I used to grease all my frame bearings, but got tired of the long cleaning process when it was time to do so. I went back to a heavy oil for all frame bearings.

I just realized that I did not answer your question.

You'll get a slighter smoother feel with greased frame bearings.

I never really noticed a difference between oil and grease feeling either connected or faster.

A thin layer of grease on the roller bearing. Oil the bearings in the cast control and the in the brake assembly.

I recommend using a heavy oil for frame bearings unless you have a tool to pack the bearings well. As far the feel, .ghoti. is right on.

A thin layer of grease on the roller bearing.

Do not do this.  A tiny bit of oil, to protect the rollers is all that is necessary.  Grease will eventually deteriorate, and gum up, causing the AR to slip.