Simsissy, the best city to play a Dynasty in is either one you're very familiar with (know location of things like special seeds and deathfish) OR one you're very very interested in playing in (helps keep you interested in the challenge). Each has it's pros and cons if the cities aren't the same ones.
Neighborhood you're familiar with
Pros: You know where the spawners are. You know who has what skill sets (namely painting, fishing, gardening, and/or cooking).
Cons: You could be tired of the neighborhood because you know it so well.
Neighborhood you're interested in playing in
Pros: Creates interest in the challenge beyond just completing it. Creates more suspense of will your Sim find the life fruit location or the deathfish location? Will they find someone to paint them in time?
Cons: You don't know where things are and who has what skills, so you're more likely to fail than in a neighborhood you know where those things are.
To me the neighborhood I was interested in playing beat out a neighborhood I knew. But for you, it might not. I personally like challenges and have a habit of making my first times doing a challenge be harder than I probably should.
