Can a trust make a charitable donation? It may seem like a simple question, but timing is everything, and if trustees don't follow the details of the trust agreement, the charitable deducation can be lost.
The underlying question in this case is "does the sale of stock in a business operating in a state where you aren't a resident obligate you to capital gains state taxes on that sale?"
The Tax Code allows you to deduct losses to the extent you have money invested in the S. If you try to deduct beyond that threshhold and it isn't your personal money, expect problems with the IRS.
A tax is a tax, but to a great extent, the estate tax and income tax stay out of each other’s way. However, there are some exceptions when there are unexpected outcomes when these two taxes intersect.
There are things that can extend (the technical term is “toll”) the collections period for IRS debt. Make an offer in compromise, for example, and the period gets tolled.