Ask a CPA

A loss is not deductible when incurred as a like kind exchange. A loss can only be deductible if you gave up unlike property as part of the exchange. The loss would be calculated as the amount equal to the excess of the adjusted basis of the unlike property over its fair market value at the date of the exchange. The loss would be reported on IRS Form 4797.

No. Business inventory or stock is considered property that does not fall with the IRS like kind tax free rules.
Generally, the other property that also does not fall into the like kind tax free rules are securities, notes, property held for personal purposes, foreign real estate, property held for sale and partnership interests.

An exchange of depreciable tangible personal property held for productive business or investment use may qualify for tax free treatment if it meets a "like kind" or "like class" test. The like class test includes 2 types. A general asset class and product classes.
An asset may only be classified within 1 asset class met to claim the like kind tax free treatment. The general asset classes may be found in the instructions for IRS Form 4562.
The product classes were designed under a coding system of the Standard Industrial Classification Manual. The manual assigns a 4 digit product class number.
Speak to your local CPA about the Standard Industrial Classification Manual or general asset classification for the like kind exchange tax strategies.

No. You cannot make a tax free "like kind" exchange of goodwill from one business to another.

Generally, intangible personal property such as a patent or a copyright can qualify as a like kind tax free exchange if the General like kind test apply.
Speak to your local CPA about the details of this like kind tax free transaction.

Generally, you have 45 days to identify the like kind exchange property and 180 days to complete the exchange. No extensions of time are allowed. The property must be described in a written document with a legal description or street address.

Report your like kind exchange on IRS Form 8824.

The sale of a residence is usually reported on Form 1099-S by the attorney at the closing or sale of the property.
It is not reported on Form 1099-S if the seller gives a written certification that the full amount of the gain on the sale qualifies for the exclusion.
Currently you may exclude from income up to $250,000 ($500,000 for married filing jointly) of Gain realized on the sale or exchange of a residence if you owned and occupied it as a principal residence for at least 2 years out of the 5 years before the sale or exchange.
Only taxable gains need to be reported on Schedule D. Form 2119 has been discontinued.

If you have a taxable gain on the sale of a residence after the $250,000 ($500,000 for filing joint return)exclusion then the taxable amount is reported on IRS Schedule D. Form 2119 was discontinued by the IRS in 1999.

You do not realize a stock gain on your exercise of stock rights. A capital gain or loss will be calculated in the year that you sell the stock.
The holding period of the new stock is as of the day you exercised the rights. The holding period will be used for the short term and long term treatment of capital gains and losses.
Your cost basis for the new stock will be the subscription price you paid plus your basis of the rights exercised.