Chris, Im a semi retired Country Lawyer AND DO NOT PRACTICE TAX LAW (highly specialized for those CPA's who became attorneys) WHATSOEVER and my legal colleauges like Mike or Dean likely have a lot more knowledge and experience then myself in this area. Also as I always post BEWARE of lay opinions especially in highly specialized areas such as tax law. Most lawyers other then tax attorneys know much about this area let alone those with no formal tax law training.
That being said and based on my limited experience with tax matters, heres my thinking.
1) Questions - if he goes to the IRS and fesses up, how do they usually settle.
IT DEPENDS on the investigator and what the dude has to offer as far as records and his story and how much liability were talking about. If he may owe hundredes of thousands of dollars in back taxes thats one thing but if its only a few thousand they arent going to expend tons of resources. No one can answer or predict that accurately !!!!!!! YES they often "settle" but theres are so many factors such as amount owed and intent to defraud and the investigator I cant put any figure or precentage on it.
2) What are the chances he gets some jail time?
Slim to none
3) Will a lawyer help, or will the IRS do what they are going to do?
A good CPA would be my first stop unless and until such time the IRS starts talking serious consequences and fines at which time Id consult a tax attorney (not A GENERAL PRACTITIONER)
Those TV adds you see are nore for high dollar tax liability issues NOT mom n pop small change.
John T Country Lawyer NOT a Tax lawyer and this opinion isnt worth much more then a lay opinion so theres no charge lol
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