Hi Michael... 
>> It's probably better to build a totally smooth and simple structured base surface 
Yes I will try to making more natural basic curve first like image below :
  
>> need a completely different approach? 
I am not come from polygon mesh modeler. 
I have SWX background that usually work with some construction curves and sketch to get the final result. 
Sometime freeform more difficult for me...
 
Thanks  
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