I don't have ideas for every point in you list but here is my way of gameplay:
[if your not interested in "perfectionating" you sims-world this may not fit, it's VERY nerdy...]
2. I like Expansion packs which gives my sims more "character". e.g. Cottage living, Island Living, Stranger Ville, Horse Ranch, Eco Life Style or also For Rent. (also some accessoires Packs are very nice for individuality.) But as atreya33 already mentioned, this depends on you own interests of course).
3./5. I love spinning wheels and similar tools, (which are often used by James Turner e.g.) for new born sims. For every new born you randomize clothing style, favorite color, aspiration and hobbies etc. As soon our sim move out you will get a new challenge for CAS, building and earning money. I never use money cheats, so if my family don't have enough money which could the next generation take to their new home it's gonna be a rags to riches under special conditions. This can end up in very funny and interesting combinations.
also 5(b).:
In my main game I started every World with exactly one couple or single sim which fits the style. I play them rotating. And at this point it really gets very nerdy, because I need a separate excel list/ family tree to manage them, especially with realistic aging. When it comes to a new generation my sims usually have children with some of my other sims. I really enjoy to watch the genetics of my sims.
So, if you're not planning to play sims in most of your free time instead spending time with family on Christmas 5(b) may be a bad idea. But the spinning wheel for a rags to riches is always nice!