I think it would be better for the player to roll however they like to play the empty hood since Newcrest itself was made with the idea of that freedom. Like if your first settler chose Athletic Aspiration let the first one be gym. If it is creativity make it Museum, food build park and grill, Deviance build Bar, Family build kids park, knowledge build library, social build lounge, nature build park with fishing pond, For fortune they could build anything but they have to had value of over $50,000.
This is just my idea to make the challenge more flexible yet still restricting rather than forcing you to build a gym for the sake of the backstory that may or may not suit all players.
I see what you are coming from with wishing for more flexibility. When I decided on a linear approach I was considering both how much more money it take to build a mansion rather than a starter and how to lure insecure builders into the challenge. Building a starter is much less daunting than building a mansion - especially for someone who doesn't really like building that much. Also, if sims are allowed to carry over funds in the Building Fund when you move to the next neighbourhood, they can build their fund faster and would not have to spend as much time getting money together when they get to the larger builds.
However, I don't see why you could not choose one of 2 options*:
1. Players do the challenge in sequence, where you start in neighbourhood 1 before doing 2 and 3. Here you always use the same household and the Building Fund would carry over.
or
2. Choose to play each neighbourhood separate. In each neighbourhood you start by creating founders, setting them down on a lot and reducing their starting funds to zero. There is no carryover for the Building Fund because each neighbourhood has a different family.
*The reason I did not initially suggest option number 2 is because there are a lot of other building challenges like this. The Drifter challenge and Block Party challenge to name a few, I wanted something different Which is why I like option 1 more. What are your thoughts?
*added later*
As for "forcing" someone to build something because it's part of the backstory, I think that one of the reason people like to do challenges in the sims is because they enjoy a framework and rule set to play in. Anyone can build in Newcrest any way they want - this challenge won't change that. It will only give people who enjoy the backstory and more guided gameplay a way to tackle Newcrest for their enjoyment.
I know this challenge won't be to everyone's taste - and I'm ok with that. My aim is not to create something that will make everyone think "yes I want to do this!", I just want to create a combined game and build challenge that will help me get this dang town built once and for all!
BTW, dodi90 thank you for commenting and voicing your views. It has made me reevaluate what my purpose for this challenge really is - and made me more sure than even that I do like the sequential setup of this challenge a lot more than the "free" version.