In the old days, one could avoid realty transfer tax by transferring the owning entity rather than the real estate itself. That one no longer works.
So, bright lawyers then decided that a two-tier ownership transfer (e.g., entity a owns entity b that owns real estate; transfer is of entity a’s stock) could be tax exempt.
It was, but that loophole has also been closed. It is unclear whether a three-tier transfer would be exempt, but that seems like an awful lot of work to go to in order to avoid a relatively modest amount of tax.
Then, the brainy guys came up with the 89/11 transfer. You transfer an 89% interest in the real property today, and the remaining 11% in three-years-plus-one-day. Now, the Commonwealth takes the position that if you are contractually bound to make the second transfer, the whole thing is taxable on the date of the first transfer.
Lying on a transfer tax affidavit to make any of the above work is a bad idea, too.
After reading the above, you might ask how the Commonwealth would know if the stock in an entity owning real property is transferred, since nothing is filed of record in any public office when that happens.
The answer is that the law requires the buyer to file a Statement of Acquisition with the Recorder of Deeds within 30 days after the transaction closes, and to pay transfer tax on the real property listed on it.
There’s a penalty of up to 50% of the tax due for failure to do so, but one might wonder (a) whether anyone actually files that form; and (b) how the Commonwealth figures it out if you don’t file it.
There is no reported litigation on this issue.