I've learned that wine can be made with varying degrees of alchohol - even in biblical times. (Drunkenness is the lifestyle that is damnable - not drinking wine by itself).
Now, I've been to countries where the water is bad. In fact, certain countries prefer bottled water (or beer) to tap water because the quality of tap water is in question. So, if Timothy was getting sick off the tap water (and was uncomfortable about drinking alchohol with meals; especially, around drunks) then Paul was helping him see the medicinal qualities of some alchohol - for the stomachs sake.
However, I believe that some wine might have helped calm Timothy down because of the stress that he had working with people. People, almost by nature, become stressed and cause stress. Have you ever worked with people, anywhere, and not had stress (worked with any type - A personality types out there).
My favorite stress people (just kidding) are controllers who would rather cause other people stress rather than look at their own issues.
Anyway, stress is a large issue with people. I don't recommend drinking at all. But I do recommend learning to deal with stressors properly.
Be the Lord's humbled . . . John A. Reeves