I referred to these questions - https://money.stackexchange.com/questions/4608/are-cobra-premiums-deductible-when-self-employed and https://money.stackexchange.com/questions/89291/can-cobra-premiums-be-paid-for-pre-tax but it was long time back.
My old job is over, employer regular coverage was till end of Oct, 2019. Starting a contract job(Corp to Corp)-self employed(sole member and owner).
Questions:
1. If i pay COBRA payments(I don't have any money in HSA for 2019)-can it be pre-taxed? Remember COBRA is not an arrangement I made - it's not an insurance from my corporation, it's something from my past job.
2. If COBRA is not pre-tax, how i can get the tax benefits? My medical expenses including premiums are not going beyond 7.5% of AGI(Adjusted Gross Income).
3. I cannot make use of my IRA funds to pay the COBRA premium as I am not unemployed for more than 12 weeks(one can pay COBRA or medical insurance from IRA if they are still on unemployment wages beyond 12 weeks)
How I can get the COBRA not tough for me financially?
The reason I am keeping COBRA is that though it costs more than 4.5 X - it is still better than exchange plans as I have already met the family deductible and only going to pay 10% of any charges. Very soon I will meet out of pocket maximum then I have to pay 0%. I cannot go for some namesake medical insurance because my family need a good one.
