Transfer of assets between companies isn’t unusual, depending on how those companies are connected (or not), however if it’s clearly being used to package up debt in one entity leaving the other with all the assets value, HMRC might be interested.
The “chocolate rental” analogy doesn’t quite work TBH. but If company A was securing business loans and buying let’s say Ferraris, then “selling them” to company B for £1.00, and in the process depriving them of VAT revenue, and being wound up with massive debts and no means of clearing them and said assets were then being used by “employees” with no discernable benefit to company B. Then yes, I reckon the authorities would be investigating.
Worth checking with companies house regarding the owner(s) of these businesses?