How make playing fun in a new world?

Every new world I have ever played or moved my sims into has been a chore. But it's meant to be a pleasant one. There are those who insist that everything has to be just right (or close enough) with a world before they will start playing it "for real," but that sounds way too much like work rather than fun to me. I usually jump right in with the household(s) I am playing and then slowly, a bit each sim night as they are sleeping or doing whatever it is they do at night, work on quadrants of the world's community lots, and take stock of the local population working again in batches make sure they have what they need and will progress/are progressing properly. At the beginning I would be most concerned that there is adequate schooling without routing issues, that sims aren't all clustering up in the same small number of careers, and that those with babies, toddlers, children, or who are pregnant have the cribs and other kiddie-related stuff they require so StoryProgression doesn't start pushing them to move houses for no other reason than they lack some furniture.

Beyond that though, it can take weeks or months of play before I ever get a world just the way I want it. On some of them I never do, they are always works in progress in some major way or another.

If at any point I am dreading loading up the game because I know that I have to "fix" a whole bunch of lots or other stuff this time and I really don't feel like it, then I have stop and re-examine my approach to whatever world it is. Again, the chore part is still meant to be fun and each phase something to look forward to.