I dont think stoicism is a lack of emotion or feeling, but a restraint in letting these things precurse irrational decisions.

In practice it can be hard to separate yourself from your emotions. It can be beneficial to start identifying your emotions in any given moment. "I feel [happy/angry/anxious,etc.]" Picture these words written out in front of you, it helps to disidentify with them. Not I am sad, but I feel sad. Then you can analyze more earnestly rationalize how best to handle circumstances.

One thing I really liked about reading about Carl Jung is that he "was not ashamed about his shame." Basically he could observe his feelings without judging himself for them.

Also, regarding insurance, adequate and cheap don't usually come on the same insuarance policy. A lot of people choose the cheaper and get upset when it isnt adequate. Try Geico, they're usually competitively priced and highly regarded. No I have never worked for them, but I have competed against them.