[verb た-form] + ら + [verb た-form] + で [i-adj 〜い → 〜かった] + ら + [i-adj 〜い → 〜かった] + で [na-adj] + だったら + [na-adj] + だったで [noun] + だったら + [noun] + だったで [verb (ば-form)] + [verb た-form] + で [na-adj] + なら + [na-adj] + で
たら~で says that if something does happen, that outcome brings trouble of its own. The same word appears twice: first as a たら conditional, then in the た-form with で – いったら行ったらいった行ったで, やすかったら安かったらやすかった安かったで, ひま暇だったらひま暇だったで.
The second half takes た, not たら or the dictionary form. It repeats only the word itself: the subject or object goes once, before the first half, as お金が does here.
With a する verb, either the whole verb or just した repeats: ごうかく合格したらごうかく合格したで or ごうかく合格したらしたで.
An い-adjective goes into its かったら form, and a な-adjective or a noun takes だったら and then だったで.
Put two side by side, one for each option, and you have a dilemma: whichever way it goes, there is a problem. The second is often the negative of the first, and the two are joined with し.
These go beyond naming a catch.
The same frame can shrug the outcome off: if it happens, you'll deal with it then. The second half often ends in ばいい.