Topic: Analyse and apply tax lesiglation

Masters Case Study

The T and A Repurchase Proposal

Taite Moneybags and his business colleague Aramis Lotsamoney are residents of the UK for 

tax purposes. They have approached you, as their tax advisor, with some questions about 

starting a business. They have an interesting business concept involving land development 


The two plan to set up a parent company, borrow money through the company structure, 

and loan the money at a commercial rate to a 100% owned subsidiary company. Their initial 

thoughts are the undertaking will encompass a 2 year planning phase, 5 years of business 

operation and then the sale of the subsidiary company. During the 5 years of operation the 

subsidiary will buy and develop land for subdivision and sale.

There are no planned changes in the shareholdings in either company in this 7 year time 

period. It is planned the subsidiary will pay interest and dividends to the parent company.

The business model involves the sale of the subsidiary company by shares to the least 

competent tender applicant and its subsequent repurchase at a significantly lower price than 

sale price after 2 – 3 years, refinancing the company’s existing loan if necessary. This plan 

requires significant initial borrowings with associated expenses including interest

The business model involves the sale of the subsidiary early in the relevant financial year 

after five years of operation. It is expected the sale will generate losses due to the

continuing interest expenses in the year of sale and the relevant years following the sale as

the loans will not be paid out, only the necessary loan commitments will be paid. The losses 

will then be utilised to maximise the time before the repurchased subsidiary has a taxable 


Formulate, with reference to appropriate legislation and case law, a concise explanation in 

the form of a report utilising sub headings which specifically addresses the following points:

1. Whether Taite and Aramis would be operating through a permanent establishment, 

and discuss the role the permanent establishment plays in determining their liability 

to tax in Australia.

2. Assuming the taxable entities involved are a resident of Australia for tax purposes 

discuss whether interest expenses will be deductible prior to commencing business 

activities, during the life of the land development business and after the sale of the 

business. In particular explore the effect refinancing may have on the deductibility 

of interest expenses after the planned repurchase, 

3. The deductibility of the expected losses after repurchase

4. Whether the fact the land is trading stock for the subsidiary means they will be 

exempt from CGT on the sale of the subsidiary

5. Identify the business risks associated with this plan and suggest some risk 

management strategies.

(Ignore GST and stamp duty issues)

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