You can drill the tank and add the sump later easily, you just cap the bulkheads.  Definately go with a drilled tank if you can. 
 
I would also get the tank drilled for a closed loop, do some searches on closed loops. 
 
You don't need the sump to cycle the tank.  But yes, you can run the sump without a skimmer for a while. 
 
When planning your sump, dont put too much flow through it, use the closed loop for the majority of your water flow. 
		
	
		
		
		
		
			
		
		
		
		
	
		
		
	
	
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