How about worst 5?
1) peak 4177 West Twin - how about a hike up into heavy moisture content and fog, where the views would be cool except there are no views now. Did you just hear a mountain lion? Weather forecast was the storm would be gone or go away but no such luck. Top it off by hiking back down the wrong ridge and then into dense bushwacking to return to the 7 or 8 mile return hike.
2) The Grotto - SM Mtns - havent gone on a popular hike in a long time? This is very good medicine. Just how popular is this? For example, try one group at 135 people and add that to a very popular hike.
http://www.meetup.com/hiking-196/events/227765683/
Admire the grotto is full of trash such as takeable maps and the smell of urine/feces. The local artists have probably painted since the last reset. Sage advice from these cats: "If you drink too much, you will not feel good the next day hahaha

". They even help on navigation, if you cant see more than 1 boulder in front of you and their mark is the only place reasonable to go to. Perhaps you could visit in the spring when the ticks swarm this place looking for dogs they will find.
3) Devils Punchbowl/Holcomb ridge - if you hear someone say this area is only for kids, send them onto this ridge from SouthFork....with a plan to return via Holcomb creek. Like decomposed rock with significant exposure? That finally sent me into the main creek on the other side, which lucky for me ended up being one of my better trips since I got to see a strange waterfall and flowers....which is either ultra rare for that area or the only one. Dont be surprised if there is no way down to Holcomb creek from that ridge without ropes.
4) Stanley-Miller via Midway ridge - you know the only reason people havent come across the trail on the old topos between Allison &SM is because they havent looked hard enough right? Make it more exciting by not being familiar with the way down.
5) Alder Gulch - everyone knows the truth about this one. People say its this hideous bushwack and you have to be 101% determined to want to see a cabin further upstream.....but the truth is they are keeping this amazing place to themselves...even going so far as editing footage? Or is it made tough at the beginning but easy going later to keep people out?