Why is perspective so difficult?

     I have been struggling with perspective for a very long time. I grew up drawing all kinds of things and for the longest time I would not do backgrounds, scenes or any piece that would require perspective. Why is it so difficult? Take a look at my recent cover of & Magazine issue 8 for example.

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     This is a typical example of 2 point perspective. The city-scape in the background uses 2 points along a horizon line and all horizontal(ish) lines converge on those two points in both directions. Still, to me it looks flat. The variances between buildings I had to work and work at, so that it didnt look like they were all in line, like blocks. But if you look at the buildings higher up they look distorted (ie. the yellow building, and the "cathedral" with the pink roof.) I have found through experiment that you have to use multiple perspective views on medieval cities, because none of the buildings are built on straight roads. (Just look at any of the OSR city maps, there typically are very few straight roads like cities we know today.)

     An example of multiple perspectives would be the foreground wall and timber-frame building with the big window. Those are on the same horizon but use different vanishing points. I am not sure this is how the master artists do this, but this is about as close as I can get. Very frustrating. 

     I am currently working on another city-scape for issue 10 of & Magazine for a city in a cave. Take a look at this work in progress (WIP). This is a concept sketch for the final (WIP) further down. I initially was going to try and pull off a Timber-frame city in a cave, but the concept of timber-frame in the moist environ of a cave just didn't work as well as what I settled on. I probably would have continued finishing this piece if I hadn't screwed up on it. Look at the center of the picture. There is a crooked tower there. My bristol board must have come un-taped from the drawing board and my building became a "leaning tower". In ink no less. I about screamed, but I learned from this mistake too. 

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     The perspective here is 2 point as well. And you can see some of the distortion I was talking about in the upper and lower most buildings. I really liked the concept of the covered bridge leading into this place and you can see I continued this in the illustration below. 

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     This one is in the works still, (and has been for weeks), I tend to leave them and come back to them often. Again this is in 2 point perspective, and I kept all the points the same here, as this is more an overview of the city. As an aside, now that I am looking at it I should have probably made the buildings in the background lighter, as the general rule is "Objects further away are light, and objects closer to the viewer are dark", but I like the contrast, and eventually the stalagmites/stalactites that surround the city will be black. 

     The only part of this that breaks the 2 point perspective is the covered bridge, which has it's own perspective. I think it works, but maybe there is a better way to accomplish it. 

     I guess the take away message here is; experimentation with perspective is the only way you will get better. Look at how other artists are accomplishing what you want to accomplish and mimic them. Get intimately familiar with the T-square and drawing triangles. Make sure you tape your work down. Wash, rinse, repeat!

Thanks for looking, comments always welcome, keep on drawing!