I have a guy that works for me part-time,..he makes a little over the limit with my pay and his other job and gets a little state help for housing,. but may lose it, btw he and he is older and not totally in the best of health yet he works very hard.,

A lot of people less deserving get much more ,.he doesn't want to apply for other public money, but he is afraid he might not be able to live in his modest home..Hes very good at what he does, but he is afraid he might have to quit me because of this.,..not sure what I would do without him,..he knows so much of my buildings

So I was wondering, in lieu of as much money, I could contribute to say,his health insurance (but I think he has medicare,).. or say, a pension plan or something simpler,,like any other benefit that might not actually count as income.

Bartering is still a taxable event so there is no difference in that and paying under the table if you don't report it.

As an employee you could require him to carry a company cell phone that the company pays for if you catch my drift. He might need to check his email for work tickets so a company provided computer would be helpful as well, oh and he will need internet at the house to be able to get to his email. If you are still game you could provide him a company truck so he can get materials and cut down on response times for emergency calls.

He has stated that he is afraid he might not be able to live in his modest home. Have a heart to heart with him and find out what his concerns are?

Taxes, insurance, utilities, cost of repairs or materials for repairs and maintenance, mortgage payments, etc.

If he makes over the limit, would he have an issue just for this tax year or would it have a longer lasting impact> How much over the limit is he is projecting? I know someone who once had to sit out the last 2 months of the year on their part-time job to avoid being over SSI limits. They then restarted the job at the beginning of the year, with hours spread out more.

Then brainstorm solutions to his actual concerns such that income is deferred, either until a more appropriate time or indefinitely.

Mike's solutions are good, also, if they allow for him to shift expenses and still meet his concerns.

Do you really want to get yourself involved in a scheme to avoid taxes and reporting what you paid to him? Do you think if he is injured on the job that he will not file a workman's comp claim on you? Or if he is caught that he will not say it was your idea and throw you under the bus?

Maybe it's time to sell your places and move the money to triple net commercial investments. If your places are in New York isn't that state making it harder on landlords? Why keep the places when they are making life harder on you?

He is part time for you, so he is going to have to cut down the hours that he works for you. That's all there is to it.

Not a scheme,..looking for legitimate ways to help him without just paying him more wages. That he could count as a benefit working for me. He has done a lot for me over the years, and he knows so much more than anyone else that works for me.

SS limits the amount ypu can earn annually and state pensions limit how much GOVERNMENT pay you can earn once you start collecting.

Mileage reimbursement works for employees, not sub contractors.

Anything you give a subcontractor should be valued and put on 1099 at end of year.

If he is an employee that is different.

I think you are asking if there is a difference between a 1099 and a 1099B. For tax purposes - nope. Now how much room do you have by giving benefits? What happens if you are audited and the IRS ask what benefits you are paying other contractors and PT helpers.