I think you are bringing up some very salient points. The Stoics do say stuff like at first you focus on things like when you break a cup or plate to rationalize it is not so bad. Then accordingly you build yourself up to things like the death of a parent, spouse, or child. Ellis even cites this example in his book.

How unrealistic! This is also a criticism of Buddhism. I practiced it for 20 years and I an attest that Buddhism is "cold" - the Tibetan Buddhists don't even have a work for love in their vocabulary.