As you can see on this SS, this map is 40 by 15 (it extends off the map.)

But I'm wondering whether or not to make this a full (say 100 by 100) map or keep it small, one street per map with each map having it's own shops, NPCs, etc....
Now, with a full city map, I could really add some realism to my city which I'm pretty big on but that means I would have many Buildings that I would need to apply Perspectives to. Like, as you can see on my SS, the Buildings in the background are cut off at the top with no to go behind them or see behind them so I don't need to worry about mapping back there as well as the same with the buildings in the foreground, although those in the Foreground disturb me just a little, because they represent the other side of the street and they can't be seen, much less entered. Or am I over thinking this?
It's just that I know I can do so much better with my maps but I need to think about which direction I should take them.
Also, Anyone notice the placement of my character's Feet? She looks like she's walking on the edge of the Tile, which only reinforces the fact that it's 2D. On one map I have that I corrected it by shifting all my Horizontal Tiles by 16 pixels to correct for that but I really don't want to do that for every Tileset. Anyone know a better way to Correct this? I tried to work on resizing my Characters but they're already touching the top of the CharacterSet and resizing loses so much detail.
The "corrected" (Shifted) Tileset.