I quit my job last year and my job rolled my 401K over to a self directed ira. Then in March 2020 I rolled it to Fidelity as traditional IRA for stock trading. In May 2020, I created another tradtional ira account with Fidelity and contribute $6K in there expecting to get a tax deduction this year, but now I want to move everything over to Roth IRA before I am moving up the tax bracket. Is it possible to roll over to Roth IRA this year. What do I need to do? And will I get penalized for it? Thank you so much in advance.
Traditional IRA to Roth are conversions which are fully taxable as ordinary income at your margional tax rate unless you have after-tax (non-deductible Traditional IRA contributions) in which case the after-tax part is pro-rated over the conversion amount and total IRA value which can result in some reduction of tax.
A conversion is not a rollover, and is not affected by contribution limits. You can do a conversion of IRA plan A into new plan C, and also do a conversion of Fidelity plan B into new plan C. As long as the transaction happens direct between the trustees (you don't get a check that you have to forward) then it does not affect your contribution limit or the 1 rollover per year limit.
The conversion will be taxable as your ordinary income rate, of course.
You could wind up with penalties if you take the money out of plan A or B as a check and try to put it in plan C on your own, and make a mistake. So just make sure the conversion is direct trustee to trustee.