Q: I've not filed Fed or State taxes for about 10 years [long story] and I wish to get current.

A: A CPA will help you get the returns, certainly, but many lack the training or background to be able to help you with the resulting tax debt. What you need is either a Tax Attorney or Enrolled Agent to guide you through that process - they can prepare returns as well. Fortunately, it's a national practice, so you can hire whoever you're comfortable with.

In the short term, you have until the IRS starts creating Substitutes for Returns and sending you amounts due letters. That could happen in months, or it could happen in years, but the IRS will be making those SFRs at some point. SFRs do not count as your filing requirement - you still have to file the returns, although they will be processed by a different IRS unit. Since you're self employed, it makes the returns and the resolution process a bit more difficult.

Once the returns are in, then you can either seek an installment agreement or an Offer in Compromise. The installment agreement is an arrangement where you pay the IRS every month. An Offer is a formalized settlement process by which there is the potential the IRS will accept less than you owe, assuming you qualify. The Offer amount is very mechanical, requires a ton of documentation, and is a bit of a long process. The IRS looks at the total equity in all the assets you own and adds that amount to your "expected future income," also governed by plenty of rules.

I would say that every month, you should set some money aside in a separate bank account to handle your tax issues. Some tax practitioners, myself included, also allow payment plans or flat fee arrangements. Feel free to contact me if you need assistance.