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Besides fighting for Baba, the Wedding Dress filler arc shows another of Gohan’s post-death gigs: serving as personal assistant to Annin as she tends her magic furnace. No wonder he doesn’t want to come back to life!
Somewhat on that note: Goku was in the habit of sleeping with his head on Gohan’s crotch, as we see when he tries the same thing with Bulma. Yep, good ol’ early DB.
While Goku never saw another human when living with his grandfather, Gohan did tell him to treat women nicely. And though Gohan didn’t teach young Goku anything of female anatomy, he did apparently explain what “bloomers” are.
Prior to his death, Gohan had trained Goku in the martial arts, including his trademark Rock-Paper-Scissors technique. Daizenshuu 7’s technique dictionary also speculates that Goku might’ve received some ki training from Gohan, which is how he mastered the Kamehameha so fast.
After this (surely the most tragic midnight potty trip in history), Goku is left all on his own up in the mountains, miles from civilization. He inherits Gohan’s magic staff, plus a weird ball Gohan found one day. Goku starts talking to this memento as if it were Gohan himself
As all this talk of kindergarten implies, Oolong is just a boy when we first meet him (though his personality makes it easy to forget): he describes himself as a “piglet” and notes that 16-year old Bulma is older than him. His official birth year is 740, making him 9 at his debut
Oolong and Puar’s schooldays are alluded to when Puar first appears, and in the anime Puar later explains that his shape-shifting skills are free of Oolong’s five minute time limit because he properly graduated (unlike Oolong, who got kicked out for panty-stealing)
The Daizenshuu dates therefore imply that the end of Slump and the beginning of DB both happen in 749, and that her RR arc cameo is about a year after Slump ends. There are a few kinks, but it works about as well as any attempt to rationalize Slump possibly can.
This is roughly in keeping with how Slump has about one year pass in-universe for every real world year that the series ran in Jump (from 1980-1984). Senbei initially claims the newly-built robot Arale is a 13-year old girl, and by the end of the series she’s said to be 17.
Arale of course is the poop-poking protagonist of Toriyama’s comic masterpiece Dr. Slump. Goku encounters her during the Red Ribbon arc in the manga (and on a few other occasions in the anime), thus putting DB and Slump in kinda/sorta/not really the same continuity, a bit, maybe.