Check out family/longer dramas, they usually tick all of these boxes. It’s rarer for the shorter form ones to have the full progression of multiple couples, lmk if you can think of any bc I’d watch too.
If you’re still open to a long one, your description is pretty much the plot of Glorious Day. There are over five couples as the show is the merging of two families, first through unwanted collective neighbor/cohabitation, then marriage through the show’s main couple (the middle daughter of the single Mom’s family to the eldest grandson of the landlord). The main couple have the full progression from strangers who dislike/misunderstand eo to boyfriend/girlfriend to married couple to parents. The other major couples are the other halves of the single Mom’s daughters: eldest does get with a divorcee, youngest with a student. Mom also ends up with her perfect match. The Parents of the ML are also a major couple who go through their ups and downs, as well as his Grandparents. Oh ML’s younger brother also gets married, although he liked the FL for a while, he moved on eventually.