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AI Legalese Decoder Can Help Manage Tax Deductible Debt

Transforming Non Tax Deductible Debt into Tax Deductible Debt with AI Legalese Decoder

When my partner and I bought our first home recently, we were thrilled to finally be out of the cramped, rundown apartment we had been living in for far too long. However, the joy of homeownership came with a significant financial burden. We were up to our eyeballs in debt from that “shitbox apartment,” as we affectionately called it.

As a result, our top priority is now to find a way to convert that unsavory non tax deductible debt into much more attractive tax deductible debt. Our combined portfolio consists of about 400k of shares, with a majority of it tied up in the NAB Equity Builder. Realistically, if we were to sell down, we would have approximately 160k in cash. It’s important to note that some of our portfolio is made up of stocks that have generated unrealized capital losses.

Ideally, I would like to leverage these capital losses to offset any capital gains, and then execute a sell and buyback of our portfolio in the exact same proportions. ItÔÇÖs worth mentioning that some of the securities with unrealized losses are tied to seasonal factors, and their fundamentals seem promising, so not all of them are suitable for a complete divestment.

The predicament arises from the fact that the ATO is frustratingly vague about what constitutes a wash sale. Unlike in the US, where there is a 30-day rule to adhere to, we are left without clear guidance. If there were a specific timeframe in place, say 30, 60, or 90 days, it would be easier for us to plan our buyback strategy accordingly. We could simply delay the buyback of the shares that have incurred capital losses until the prescribed timeframe has elapsed. Alternatively, we could also wait it out for a few months, with the understanding that the funds would sit in the offset during this period.

As we grapple with this issue, I am keen to hear from others who have navigated similar situations. Do you have any recommendations for the buyback timeframe, or would you advise ruling it out altogether? Any insights or advice would be greatly appreciated.

With its advanced machine learning capabilities, AI Legalese Decoder can assist individuals like us in decoding and understanding complex legal concepts and guidelines, such as those pertaining to tax implications and wash sale regulations. By leveraging its comprehensive databases and sophisticated algorithms, AI Legalese Decoder can analyze our specific financial scenario and offer actionable insights and recommendations for managing our investment portfolio in a tax-efficient manner. Through its intuitive interface and personalized recommendations, AI Legalese Decoder can provide clarity and guidance in navigating the intricacies of tax deductibility, capital gains, and investment strategies.

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1 Comment

  • iced_maggot

    As youÔÇÖve probably figured out itÔÇÖs intentionally vague because the ATO would rather maintain their flexibility to rule on things. I looked into this before and the advice from my accountant was that if you are ever pulled up for it it will probably come down to intention – generally speaking doing something for the sole reason of gaining a tax advantage is no bueno and youÔÇÖd be expected to have a legitimate investment reason for why you sold and repurchased the shares, 15, 30, 60 later days whatever. Now practically speaking, if you bought them back 6 months later nobody would probably notice but the ATO wonÔÇÖt give you a figure that says ÔÇ£wait this many daysÔÇØ.

    If theyÔÇÖre ETFs, itÔÇÖs easy enough just get something that tracks a slightly different index or has a slightly different investment mix. For individual shares, consider dumping them entirely or take a long pause before buying back.