Do you hold yourself from spending what you have to the point of depriving yourself of what you deserve?
No because that is slavery of oneself. Slavery is dehumanising and to give yourself such a treatment is just worse of it all, why deprive yourself of what you can afford? That means you suffer or labour to make money and you also labour to eat from same money, that is bad. Money is meant to take care of our challenges whether direct financial or indirect, money is important.
Do you keep significant savings for occasions that might only happen in your imagination?
It may not be intentionally. That is when you don't have financial challenges then you can save but if you do then you can't save if you barely survive with the little you earn.
Or at what point would you allow yourself to be drained of your last penny?
Health and medical issues because it involves saving of life and that is why they say health is wealth. If you are alive then you have hope of being wealthy.