This question is a good question but you really need to hire a lawyer to advise you on that. Some annuities are very different than others....

First, the questions you raised are complex and the answers are best resolved by hiring a tax attorney to guide you rather than rely upon website...

First, there should be an LLC operating agreement which limits transfers of member interests subject to right of first refusal by the other member...

MA doesn't have a gift tax to donors & donees don't pay any gift or inheritance taxes from anyone. The IRS also doesn't tax recipients of gifts or...

We would need much more facts to answer that correctly but generally the answer is no. I suggest you or the employer reach out for tax advice...

I know you view this as a "side hustle" but the IRS and MA DOR will simply view it as a business. When you buy sneakers you are required by law to...

This is not a tax question, but because you ended up with a loss on your Schedule C, it should not affect your benefits.

Most payment agreements with Massachusetts provide for an unlimited waiver of the statute of limitations. But your agreement is an older one, so...

Yes, he must file his own returns for federal and MA. The trust can pay taxes or it can pass the income through to him [to save taxes].

This question should not be answered for you without hiring a tax lawyer to help you at least with some guidance. If the paystubs you received...