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1. No, it shouldn't. In fact, having a nice flat side (presumably you are going for rectangular bases?) will actually make it easier to measure turns. The only issues basing could have is if you play on boards with a lot of terrain that forces you to squeak through choke points, or find yourself clustering your ships tightly together. Even so, these issues can be minimized by keeping the bases as small as possible.
2. I haven't done this for any of my DW models, but I have based a number of naval miniatures for other games. It is pretty easy to do:
-Cut the base for your ship out of the material of your choice ( I recommend sheet styrene/plasticard).
-Paint the base your preferred color of blue. Also include any wake details you want to include at this step.
-Glue the mini to the base.
-Coat the base in water effects. This is a white-ish paste that will try clear and shiny, and is made by several manufacturers (GW, Woodland Sceneics, Vallejo). It is also thick enough to shape into waves and the like.
-As a final optional step, you can dry-brush the water effects with a little white paint to get some white caps if you would like.
You could probably go without the effects, but it really makes the the whole thing stand out.
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