“I have been where you are at - paralyzed by fear that my return wouldn’t be perfect.”
“The thing I have learned is that tax returns aren’t as perfect as e would like them to be. Just organize your records the best you can, and start working on the return for the earliest year. Write down notes of what you do and decisions you make. Make a decision and move on...there is no way your return will be perfect....just do the best you can and file.”
Excellent psychological advice..... Most conservatives are really good people who care and want to follow the rules. They really beat themselves up when they think they may have broken the rules.... The fear is turned internally and used as a self torture tool. Know that all will be ok and that prayer does help.
I’ve worked with hundreds of situations similar to yours and worse. There is always a solution and when you address it proactively rather than adversarially, it usually goes better.
Although now retired, I worked as a liaison for all the CPA’s in our state as a member of the CPA Association Federal Tax Committee working with the IRS to resolve problems. At one of our meetings with the IRS, a senior regional IRS manager said to us, “We need your help as occasionally some of our agents wonder off the farm and we need your help to reel them back in.”
These agents are human beings and usually will work with people who are trying to solve a problem. They will bend over backwards to help you find the best solution within the law. My experience is that they are so used to being in an adversarial relationship that you should only show your cards to a CPA or enrolled agent as your advocate.
Don’t let shame shackle you.