only because it is Friday....
technically, the initial premise is incorrect.
suppose you are sitting on Short Line railroad, just 5 squares from GO, collect $200.
you roll a double 3, but that is the third double in a row so you go directly to jail. do not pass GO, do not collect $200. that is the rule of Monopoly.
the regs are similar, if you don't pass the gateway, that means you never went through the gateway. you never reach nondicrim land. you can't collect $200. Wasn't the IRS clever for choosing such a descriptive word like 'gateway' to describe things. Well, ok, maybe clever is giving them too much credit.