Citizen App. & Tax Issue

[RM1101]

I obtained my PR through marriage and it will expire toward end of next year. I plan to apply for my citizenship this year. I am still married, we file our taxes married separate. Here is my issue-My last 4 years taxes are filed and up to date. But I irresponsibly didn't file my taxes between 2008-2016, no good excusable reason. I just had these done and mailed last week. CPA told me my bill after fines & penalties will be about 22k. I have 18k toward this and plan to setup a payment plan for the balance. He said it will probably take about 2-3 mos. for IRS to go through everything and send me demand letters. I can't help thinking back to wonder whether I should have filed for the citizenship before mailing in the back taxes as the last 4 years are up to date.

-How bad are my chances of getting the citizenship (or even GC extension should this be a better option) approved or rejected?
-What would you advise I do-would you recommend I go ahead and mail in the application now before the IRS letters arrive, wait until I get them and enclose them in the application? Or,
-Generally what should I do next?

P/S
Other than the above I don't have tickets, arrests or anything, nothing.

 

[SusieQQQ]

Just to settle your “I should have filed before” regret, no, because one of the questions on the form asks if you have ever failed to file taxes, and asks if you owe taxes. Answering yes to those questions without a payment plan in place would have been a problem. I would personally wait until there is a formal payment plan in place before filing so that you can state that in the explanation section for this question. If your FO is one with fairly long processing times, you may want to file now anyway, in the explanation say you are in the process of arranging a payment plan with the IRS, and then (assuming this is organized before the actual interview) show the details of the plan at the interview .