The first thing I would do is find out what they think is friendly and what is "cheesy" by whomever you are playing against standards. Use the friendly list in all your friendly games and use a competitive list for any tournament games. A majority of the time your friends or opponants will want to play the competitive list out of tourny so they don't get stomped come tourny time.
As far as cheesy goes, I think of it as a balance thing. 1000points I don't think there is a place for a dragon,or cairne wraiths. 2000points I don't think there is a place for 2 steam tanks and karl franz or any of the "uber special characters" (Archaon, Karl Franz, etc. etc.) 3000+ points though I would just go No holds barred, that is what makes 3000+ fun IMO. Generally I would just think about "can my opponant reasonably handle this?" if you are caring about being "cheesy" or not.
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