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No the real issue with the insane unfair challenge is its a war of attrition. You need to keep your units alive long enough for that next big heal and kite like mad when you need to.
I took a fairly balanced team (cyclops+4 humans) to the Pit and ended in final round first try. My team could handle most teams, until my frontline cyclops died in a sustained battle against their cyclopses and cupcake.
I bested the Pit with my 2nd try when I replaced a human with a low lvl Spidaur which fortunately leveled up very regularly. I would've died again if my Spidaur didn't level up when she killed one of the final problematic targets (tank human). So my remaining 2 humans and Spidaur could hunt down the remaining squishy targets.
My biggest issue with the Pit weren't the enemies themselves, but the RNG of each round (2 cyclopses or kobolds were really annoying) and sustaining my team without a cupcake.
For that reason, if you want to guarantee beating the challenge, bring a well-rounded team and AT LEAST one cupcake. While troll moms are great, you can end up in a bit of a bind if a team appears with lots of AOE/fire (and rainbow horses are pretty common in the Unfair challenge, and on the insane setting they can appear as elites with much improved accuracy!).
My standard set-up now (2 tank humans with shields, 2 spidaurs, 2 cupcakes) hasn't lost a fight in the insane unfair challenge in ages, and sometimes I even leave it on auto-battler while I AFK. I really recommend at least one cupcake because there's a terrible round 3 team that will literally devour you if you don't enter that fight with decent levels of health (I'm thinking of the 4 vamps + 4 zombie team here).
Test 1: Went well until Round 3 with a team with four pixies
Test 2: Actually won
http://steamcommunity.com/sharedfiles/filedetails/?id=1335360159
Verdict: Turn on auto-battler and let the game run itself and it can also be a fast way to grind xp