I got $100 on it

Why not just let Kaufman write the script for Monopoly? Just make Uncle Pennybags into an ennui-ridden artist type who thinks about nothing but himself and death, and then through some bizarre and improbable circumstance becomes involved in a surrealistic dash to acquire properties. Allusions to postmodernist literature (maybe intentional maybe not) and philosophy of mind will be made along the way, but while building hotels that have smaller hotels within them (or something). The film will end with Pennybags miserable, alone, trapped in his own mind, dead, or some combination of these. If we're lucky, though, instead of a soul-crushing profession of nihilism, we will just get a vague and unsatisfying non-ending - an endless recursion of passing Go, if you will.