if you downloaded a plugin for free thats not free

If the plugin is free no, if you have paid and didn't have distribution rights yes.
 
If you bought the plugin it depends on the rights that come with it. The same applies to templates. Its up to you if you want to the violate the rights or not but I would not recommend it. If the buyer of your site gets into difficulty because of plugins you have illegaly given away then you could find yourself in hot water.
 
What if I try to flip a site using a paid plugin obtained from a "less than reputable" source? Can the buyers tell the difference? Do I get in trouble?
 
Never let your buyer to face the problems in future, remove the paid plugins (depends on the terms of it like shadysays said).
 
If the plugin's license permits one copy per person, you should remove it or offer to purchased additional license for the new owner. If the license is per-domain, the license is transferred along with the domain so nobody gets in trouble, but you can't use this plugin anymore unless you pay.
 
The best, for me, its to download programs who cost cash and just take a crack for have the full version :)
 
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