Ruby Jewel
I don't buy into many of the "pre-packaged" story lines in decks with illustrated minor cards, so I'm open-minded about different ways to view the 5 of Pentacles. Usually I follow elemental, astrological and numerical correspondences. In this case, Five causes disruption in mundane routine, "rocking the foundation," so to speak, like an earthquake) while nimble, footloose Mercury in plodding, conformist Taurus suffers mental anguish due to being completely "out of its element:" the dilemma won't be resolved entirely by "mind-over-matter" finesse; some "heavy lifting" is implied. Crowley said that this card (titled "Worry") has the effect of intense strain coupled with long-continued inaction, a "Damned if you do, and damned if you don't" kind of situation. The "hidden desire" may simply be to make all of this profound anxiety go away as quickly and painlessly as possible.
I agree, the illustrated pips have bred all kinds of speculative meanings for these cards. As a matter of fact there seems to be no limit. Of course when one thinks of worry in connection with Pentacles, that becomes pretty specific. If you have known real poverty, then you know the "trap"....there seems to be no way out because poverty breeds poverty...and you worry, but you are damned no matter which way you turn. Just look at the homeless with no phone, no shower, no clothes, no car....no place to sleep....how would you ever wake up in the morning and go to a job or for that matter find someone who would hire you? I can see this card as a card of financial desperation and depression, with no way out....the only hope being the church where at least one's spirit might find reprieve. On a more typical (hopefully) level, the idea of "worry" is equally appropriate. The word makes a good 'handle' for the card. Like the entire tarot, there are as many layers of meaning as there are layers of worry. But at least "worry" makes a good starting point to address the issue in matters of "layers" of depth. The problem seems to be created when the definitions begin expanding laterally......like concentric ripples in a pool of water to encompass any kind of worry or problem one happens to be experiencing at the moment. Five of Pentacles is about finances. Cups cover matters of the heart.