Retirement tax questions

@macuser_22 @dmertz   Thank you so much for your input. I apologize for repeat questions, I should have compiled it into one thread but I had more questions as I read into this situation.

I honestly do not remember what I exactly did for 2018 but that for that year I was walked through with a CPA with screenshare so I hope everything was done correctly. I do remember having to look up a sample statement for recharacterization and putting a statement in there so I believe this was done correctly.  Is there a way to check this on my 2018 return?

On my Form 8606 for 2018:

Line 1: $1000

Line 2: 0

Line 3: 1000

Line 14: 1000

All other lines are blank. 

Reason why there are 2 different 1099's for conversion is because for tax year 2018, I was with a different brokerage and I had done $1000 recharacterization and conversion in 2/2019, and for tax year 2019, the current brokerage issued another set of forms for this year's recharcterization and conversion.  Had I stayed with same broker, I believe the total conversion amount would show $7286 on one set of 1099...

I had no idea my Step 3 was wrong, thank you for catching my mistake!  I have just removed all the entries and now am going to add Roth IRA first, and then Traditional IRA as @macuser_22 mentioned.

 Checked Roth IRA box ONLY

1. "Tell us the Value of All your traditional IRA accounts on December 31, 2019" 0, since all the funds were converted by that time

2. "Did you make a Roth IRA contribution for 2019?" Yes

3. "Is this a repayment of a retirement distribution?" No

4. "Enter your roth IRA contribution" 3000, since that was the amount originally put in then was recharacterized along with gains

5. "Switch from a Roth to a traditional IRA?" YES

6. "Tell us how much you transferred" 3000, gains are not put here, right?

7. I put in statement explaining the situation of recharacterization and conversion "On 11/25/2019, I recharacterized $3268 ($3000 original contribution + $268 gain since original contribution date) from my Roth IRA to Traditional IRA. I contributed $3000 additionally into my Traditional IRA to meet maximum annual contribution limit of $6000. On 12/5/2019 I converted the full amount of the $6268 in my Traditional IRA ($6000 contribution, $268 gain) back into my Roth IRA"

8. "Let us track your Roth IRA basis" Yes

9. "Withdraw from your Roth IRA before 2019?" No

10.  "Enter Prior year Roth IRA contributions" 21000, since I have contributed 2015, 2016, 2017, 2018 (5500 * 4) 

11. "Any Roth IRA Conversions before 2019?" Yes

12. "Tell us the years" 2018, for the $1000 that had to be converted

13. "Enter 2018 Conversions" 2018 Taxable conversion is 0, and 2018 Nontaxable conversion is 1000, right? Since I've already paid tax on that 1000 that I had originally contributed into Roth?

14. "Adjust Roth IRA due to divorce?" No

15. "Any Excess Roth Contributions?" No

16.  "Choose Not to deduct IRA contributions" Yes, make part of IRA contribution nondeductible, and I put 6000, since I contributed additional 3000 to my traditional IRA on top of the conversion to fill up annual contribution limit and converted whole 6286 (6000 contribution and 268 gains) to Roth IRA

17. "Your IRA Deduction Summary" 0 deduction applied

Then I went back into the IRA data input and I found both Traditional and Roth IRA boxes checked. I clicked continue and:

1. "Did you contribute to Traditional IRA?" Yes

2. "Is this repayment of a retirement distribution?" No

3. "Tell us how much you contributed" only 3000, since the instruction says "do not enter roth contributions even if you later recharacterized them to traditional IRA,", and 0 of it was contributed between january 1, 2020 and April 15, 2020

4. "Tell us how much you transferred" 0, since this is asking for recharacterization, not conversion

5. "Any excess IRA contributions before 2019?" No

6. "Any non deductible contributions to my IRA" Yes

7. "Let's find your IRA basis" 1000, per line 14 for 2018 Form 8606

8.  "Tell us the value of all my traditional IRA accounts as of December 31, 2019" 0

9. "Is this repayment of a retirement distribution?" No

10. "Choose not to deduct IRA contributions" I selected Yes, make part of IRA contribution non deductible, and here I put whole 6000, right? 

I believe now things are correctly put in for the Deduction and Credits section. It shows $6000 for 2019.

Now for Income and Expense section, I need to enter the 1099-Rs for the distribution and conversion for tax years 2018, 2019...  What makes it more confusing is that I have 2 sets of 1099-Rs because I was with another brokerage for the recharacterization/conversion for 2018 than for 2019 as explained earlier... Am I supposed to enter only the Roth IRA 1099-Rs or both of them?  

Once again, thank you @macuser_22 and @dmertz for your help... I really appreciate your time reviewing my question.