Controlled Experiments.  Try shaving daily WTG for a week and see what happens.  If it's comfortable and close enough, then you're good.  If you think you would like it closer, try going ATG for a week and see what happens.  Then go from there.  The number of variables are pretty large, so it will likely take some time to settle into what works for you.

Razor type - I've switched to a DE Safety Razor for cost and comfort reasons.  Many people are perfectly happy sticking with cartridges.
Passes - 1, 2, or 3 are the most common.  With the Grain, Across the Grain, or Against the Grain.
Prep - Shower first, shave in shower, beard softening products, soap or cream, etc.
Finish - AS or no AS?  Witch Hazel?  Moisturizer?  etc.

I would love to be able to shave ATG daily.  I haven't figured out a way to do it comfortably yet.  I currently settle for a daily 2 - 3 pass shave WTG and XTG that is comfortable, and close enough.