Work for cash and live off grid

Just follow this simple two-step plan:

Step 1: be super wealthy Step 2: be jewish

It depends on how you make money. Hard if you get a W2, relatively easy if you own your own company, complicated but worth it if you own a large corporation and simple if you answer to the name Pelosi.

Risk and reward balance. I despise paying tax to an entity that hates me. Dodge tax within reason. I'm waiting for a 'tax revolt' thats been creeping for a long time.

If you're serious, the only answer I can provide is don't engage in tax evasion.

Instead, do everything you can to legally reduce your owed taxes. Live in a low-tax/no-tax area with great homesteading and homeschooling laws. Grow your own food, trade with locals for other things you need. Get a knowledgeable tax professional who will help you plan to maximize your deductions. Yes, a great tax pro is going to cost some money, but what they can wind up saving you (especially if you are a business owner) more than pays for their fees.

Be your own boss if you can, as well, and keep all your receipts AND keep good books. Good bookkeeping is the foundation for a great tax pro to maximize your deductions. (And don't make your business cannabis. The taxes involved in cannabis are absolutely insane.)

Evading taxes is illegal, and advice on how to do so is being a part of a conspiracy to commit a crime. There are plenty of legal tax loop holes (minimal taxes on capital gains, real estate gains, tax advantaged retirement accounts). Rich people avoid taxes legally.

Proper way to phrase this could be, How likely is giving weekly financial help to someone else to be mistaken by the IRS for tax evasion, and what ways can the chance be reduced?

Depends how well the government has you documented. If you're communicating on the web then you are probably pretty well documented.

> Anyone who answers this on how whether reply, or DM is a idiot.

In the past it generally took a while for the IRS to catch up with non-filers. I know of a guy who didn't pay in for years.. no fed, no state. A couple of years ago he went to buy/registered a new car with the state. Apparently this was enough for the state to realize he hadn't filed, soon after the state went after the guy, the IRS auditted him.

Rumor is the IRS is dedicating more effort now to go after tax evaders, so who knows how effective they will be.