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All right, after spending some time very quickly going over the list of challenges on the boolprop forum, I have made a list of the challenges I would like to try and complete as I go through my learning on the various expansion packs, which means, unless it is a one generation challenge, most likely only one challenge will be done per expansion pack.  What I am trying to figure out right now is what order I should do them in so that the challenge best matches up with the additions the expansion pack added.

List of challenges I would like to complete eventually - Original List:
  • Legacy Challenge - Base game - in progress
  • Alphabet Legacy
  • Apocalypse Challenge - Nightlife
  • Officially Wacky Boolprop Challenge - University?
  • Asylum Challenge
  • Build a City Challenge - Apartment Life
  • NPC Challenge
  • Prosperity Challenge
  • Pure Entrepreneur - Open for Business
  • Royal Kingdom Challenge
  • Who Is Your Daddy Challenge - Free Time
There are more challenges than expansion packs and that is because some of them, while fun I am sure, are more limited in what they would require for exploring the game so the short ones might get played at the same time as a longer challenge.

You may be wondering why I am doing this now since I am not even on to the second generation of my Base game Legacy challenge, well, I am a planner, I love to plan.  If I have a list now, then I will be less likely to try a challenge before I have enough expansion packs added to complete all of the challenges and I won't put off one until much later that could be done easily earlier on.  Also, since I have only read stories for a few of these, I may not fully understand from just browsing the list and rules, what really is needed to make the challenge fun and interesting.

All help is always appreciated.

Modified list as per suggestions: 

  • Legacy Challenge - Base game - in progress
  • Asylum Challenge - University
  • Royal Kingdom Challenge - University
  • Apocalypse Challenge - Night Life
  • Officially Wacky Boolprop Challenge - Night Life
  • Pure Entrepreneur - Open for Business
  • Alphabet Legacy - Pets
  • NPC Challenge - Seasons
  • Who Is Your Daddy Challenge - Bon Voyage
  • Prosperity Challenge - Free Time
  • Build a City Challenge - Apartment Life
 
 
 
 
 
 
Mmmmm challenges *Homer-like drooling*

I haven't tried all of them so I can't advice you much, but I can still give you my two cents.
The OWBC can be done with any number of EPs but I'd suggest you have at least two EPs so you can get as many points as possible, so I'd say you should try it once you have Nightlife as well as Uni. (Nightlife comes after Uni, doesn't it?)
The WYD challenge can be done even with only Base Game, there are plenty of potential babydaddies to choose from really, but of course the more the merrier.

lol, you and your lists. :D
Yes, I am a list fiend, I get it from my parents, you should see my dad make lists, seriously, I aspire to his level of listness; I don't think that is a real word.

Maybe I will move OWBC to Pets since I want to avoid that particular part of the Apocalypse rules. Although I think I could do an Apocalypse with just University since you really just have to have University at the beginning. I may swap those two.

I guess when I saw the list of baby daddies needed for WYD my eyes kind of bugged out of my head and I couldn't figure out where I would find them all if I did it too early. I think Vacation is about as early as I could do that one but I will go back through the list later when I am a little less tired and and can figure out who comes from what expansion pack.

Thank you for the suggestions.