Each year I am faced with the same conundrums:

Issue 1:  If the days of repentance and reflection start with Rosh HaShanah, what happens to the bad things you do between Rosh HaShanah and Yom Kippur? 

Example:Let’s say I see someone in a horrible outfit at synagogue and, over Rosh HaShanah lunch with the family, I discuss the sartorial transgression in all its gory details  This is technically a sin (because it is gossip, aka loshen hora).  

Quandary:  Do I need the chuvah (repentance/atonement) ambulance or am I in a chuvah-free zone?

Issue 2:  Why shouldn’t we shower and brush our teeth on Yom Kippur?

Example:  If you have one date with G-d each year and you are begging for another year of life, shouldn’t you look and smell good?  My mother would not let us out of the house without lipstick on a regular date.  And this one is with the Almighty. 

Quandry:  With everyone getting back to basics, do you think bringing a burnt offering is a good idea?

Issue 3: Based on my observations, is the rule on Yom Kippur no animal skin on your shoes but not your purse or belt?

Example:  Let’s say you see someone wearing canvas shoes (because no animal skin on YK), and you notice that the person is carrying a leather bag and wearing a leather belt.

Quandary:  Do you say, “from one animal killer to another, nice belt and shoes”?