A believable chi chi romance H game, IMO, should take place after Perfect Cell Saga but before the Buu Saga.
Chi chi is a widow and Goku has been out of the picture for years. Chi chi needs time to heal, and while some widows may never find another partner, for the sake of an eroge, 2 years after Goku's death would serve nicely.
This gives the H game MC a cool 5 years of peacetime to make their attempt at her heart.
As a clear departure from Goku, the MC could be just a normal guy who moved to Mt. Paozu to get a break from the hustle and bustle of the city.
He purchases a plot of land nearby Goku's old house because it's the easiest place to build a home since there's already people living there.
And so, the game story will center around the MC player doing their best to help out Chi Chi and her family, and making choices that allow him to worm his way into her heart. Until she finally caves in and gets with the MC.
Of coarse, what fun would it be without conflict? The player will also have the option to interact with the other DB characters.
Helping them could help unlock items that could help unlock new sex positions, outfits and story progression.