If you haven't browsed through the Dundjinni forums, you really should. There are hundreds of good user-created map objects available for download there. http://www.dundjinni.com
The presence of the well would probably cause the road to widen there--it will attract lots of traffic, and carts will have to divert around it. Also, if you add any additional buildings, especially houses, they'll tend to cluster around that well. The people will be going there at least once each day, so they'll want to build their homes as close to it as they can to reduce the distance they must walk. Businesses, especially the ones that cater to travellers, will still favor the main road(s) through town, though.
It's looking a lot better already.
Oh, and don't worry about double-posting. I do it all the time and nobody's chastised me yet! It is possible to edit your own posts, though, if you just have a small correction or addendum.
And finally, that was Torstan's advice, regurgitated by me.