Thanks Critter! (Love your pic!!)
My former employer did not reimburse me for anything, which is why I a confused about them sending me a 1099. I had COBRA insurance through them for a few months after I left the company. I paid the premium to my former employer and they then paid the insurance company. The company is small and fairly young, and I am probably the first employee who ever got COBRA. I can see them being confused, just as I am.
I think your option #2 will work best for me. I appreciate your guidance. This has been an especially challenging tax year for me (left the job, sold the house, moved out of state, started a new job, sold stock, bought a house...). I have very little brain matter left to use for taxes. (haha) 🤔
UPDATE: Option #2 was successful.
