Seasons definitely helps with skilling; Sims do homework and learn skills faster in Autumn.

I check their one true hobby and then research what jobs suit those hobbies

I've decided to implement the rule that any sim that graduates high school with a failing grade is only allowed to work in a player-owned business. They can open their own if they want, but otherwise the best they can hope for is Manager. Slacking off should have some real (sim)world consequences.

Well, first of all, rabbit hole jobs are boring. So I try to do without them as much as possible. Owned businesses, writing novels, selling paintings, busking, farming, crafting -- all are much more interesting ways to make money, and all will start to snowball at a certain point, past which money becomes a non-issue.

Depending on the neighborhood and the rule set in use, though, there may be reasons to get one. I give LTW jobs due consideration. But there may be "illegal" jobs. You can't be a professional gamer in a neighborhood where it's supposed to be 1901, for example. If the town is small and isolated, with no Downtown, there'll be no call for the Intelligence career. So I have to take everything on a case-by-case basis and adapt the case to the neighborhood, or the neighborhood to the case, as appropriate.

Before my Strangetown imploded, I got so many Fortune sims who wanted to be Hand of Poseidon that I added a subhood with a lot of beach, which I declared to be on the Inland Sea (Great Salt Lake is an inland sea, so perfectly reasonable), and named it Research Beach -- only families with Oceanographers could live there, and I even went so far as to change the careers of apartment neighbors to Oceanographer. (I am totally doing a variation on this theme, sometime, in a hood that isn't about to die and gives me a chance to actually play the concept).

In the 1901 neighborhood, I'm using the job stoppinator extensively, because people without college educations can get into certain careers but shouldn't rise too high in them, and because, though I'm not modeling real-world classism, racism, and sexism too closely, I am applying a glass ceiling as appropriate, and if I want to play this hood through the century I need to restrict some things so I can simulate social changes. When/if I ever get up to the Great War, every man of military age will have to quit their jobs, join the military, and be deployed overseas using the prison system, and some jobs will open up for women that hadn't been available before; then the men will come home and crowd them out of some jobs, while others will have permanently become female-dominated. At the moment, women from the right side of the tracks can work for their families but should not have rabbit hole jobs, and if they do get one of the handful of respectable ones, will need to quit when they get married; women from the wrong side of the tracks will be more likely to work outside the home if they can take a break from having young kids or arrange their work hours or have a child minder (not the nanny! Apartment neighbors or an unmarried relative or something). As the century advances, women from the right side of the tracks will have wider employment opportunities, but will still be expected to quit on marriage till the 60s. And so on.

Back in good old Drama Acres, if anyone had an LTW career I got them into it, looking through the paper/computer every day till they found it. If they didn't, but needed a steady income, I generally looked at the paper or newspaper once, took the most lucrative offer, and called it a day; that was what they did for the rest of their lives, however odd it was. That's how I got Family sims who were movie stars.

For some careers, I've gradually instituted some common sense restrictions across neighborhoods. If you have a Hall of Famer or World Famous Ballet Dancer LTW, you'd better hope those jobs turn up in the first week of adulthood (I don't do teen jobs; teens need more free time, not less, in real life and in sims!), because those jobs have physical demands that mean you need to start young. No college degree, no Scientist, Medicine, Natural History, Oceanographer, etc. -- but that isn't often a significant consideration, because I love University play and most of my sims get degrees. Or a neighborhood may modify it, like the 20th-century neighborhood described above.