Thanks, hazelnut. I would want to start with a founder (Midnight Dreamweaver), so I'd have to get a cheap house. I don't have the thing that lets us turn off expansions. I can see the wisdom of setting it to summer constantly, though. And, true, I wouldn't be able to go without my cats!
Pam, if it makes you feel any better - I was petrified of this challenge for a long time. I thought "this looks way too complicated for me!" Then after I completed my Life States Dynasty, I felt like I just needed a project to work on that would challenge me and interest me - so I decided to come back and look through the rules and honestly they're not that bad! In practice it's much easier than it looks. I keep a notebook in front of me with all the rules (and regulations - especially the ones I would be silly enough to forget!) and another notebook with a loose strategy. I first thought of all the skills I would want to use and spread those out, then I thought of which towns might best be suited for those skills, then I laid the towns out in order that I would use them and arranged the skills to each generation accordingly! I also did this with careers. Using Twinbrook to knock out my Professions that would be needed there, Isla Paradiso for my Scuba Diving and lifeguard career, and so on.
You're very good with challenges, so I have no doubt that what you do will turn out wonderfully!
Also, for starting with Midnight, you can bring in townies to help you out with money in the beginning. Honestly though, money is the least of my problems in my file (I'm still in world 1).
I just recommend having a backup plan if all else fails!