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Can I beat ChatGPT in picking great dividend shares to buy?

How good is AI when it comes to picking dividend shares for the next five years? Stephen Wright is on a mission to find out.

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I asked ChatGPT to pick me a portfolio of five UK dividend shares. And just to make things interesting, I’m going to compare that with a portfolio of five income stocks selected by me.

Starting today, I’ll track both, see what happens, and report back with the results in due course. I’m not putting my own money behind what ChatGPT says, but I’ll be keeping score.

Should you buy Aew Uk REIT Plc shares today?

Before you decide, please take a moment to review this report first. Despite ongoing uncertainties from US tariffs to global conflicts, Mark Rogers and his team believe many UK shares still trade at substantial discounts, offering savvy investors plenty of potential opportunities to learn about.

That’s why this could be an ideal time to secure this valuable research – Mark’s analysts have scoured the markets to reveal 5 of his favourite long-term ‘Buys’. Please, don’t make any big decisions before seeing them.

The portfolios

Right then, let’s get to it. The rules are pretty straightforward – dividends are reinvested back into the shares of the companies they came from and the highest total return wins. 

With that in hand, let’s get to the portfolios. Since ChatGPT gave me suggested weightings for each position, here are both portfolios with percentage allocations for each choice:

ChatGPTStephen Wright
British American Tobacco (22%)Admiral (22%)
M&G (22%)Games Workshop (22%)
Shell (20%)Croda International (20%)
Unilever (18%)Diageo (18%)
OSB Group (18%)AEW REIT (18%)

In both cases, we’ve mostly stuck to the FTSE 100 for ideas, but each team has an outsider. ChatGPT’s gone for OSB Group (LSE:OSB) and I’ve selected AEW REIT (LSE:AEWU).

Having seen the teams, I’m feeling pretty good. But I didn’t expect to see OSB Group making the list, so let’s have a closer look at the wildcard on Team ChatGPT.

OSB Group

OSB’s a specialist mortgage and savings business. It works a lot like a bank – taking in deposits, making loans, and earning a profit on the difference between the interest rates.

It specialises in loans for Buy-to-Let investors, developers, and commercial properties. Its focus in this area can give it an edge over more general competitors in terms of assessing risks.

Its lending margins have been pretty strong, but they’ve been starting to come down recently. This is due to higher interest rates increasing funding costs, which is a risk worth noting.

At the moment though, there’s a dividend yield of around 6% on offer. But while I’m interested in taking a closer look, I don’t think I like it as much as anything I’ve chosen.

AEW REIT

The wildcard in my portfolio is AEW REIT – a real estate investment trust (REIT) that doesn’t play by the usual rules. And it could just be the ace up my portfolio’s sleeve.

Please note that tax treatment depends on the individual circumstances of each client and may be subject to change in future. The content in this article is provided for information purposes only. It is not intended to be, neither does it constitute, any form of tax advice.

Conventional wisdom says REITs are supposed to focus on properties with long-term leases in high-demand industries. That’s the usual way to try and achieve consistent rental income.

AEW focuses on unpopular sectors where demand’s weaker, but supply’s also low. And it looks for leases that are closer to expiry as potential opportunities for rent increases.

It’s a high-risk strategy with a much higher chance of vacant buildings. But the company’s executed incredibly well on its strategy and I think income investors should take a look.

Smart money

This particular competition is just for fun. I’m not willing to put my own money behind a portfolio generated by ChatGPT, especially when it contains a name I don’t know very well.

I am however, interested to see how the two portfolios get on. I’ll set up a simulation using my broker’s online platform – watch this space for future updates.

Stephen Wright has positions in Diageo Plc, Games Workshop Group Plc, and Unilever. The Motley Fool UK has recommended Admiral Group Plc, British American Tobacco P.l.c., Croda International Plc, Diageo Plc, Games Workshop Group Plc, M&g Plc, and Unilever. Views expressed on the companies mentioned in this article are those of the writer and therefore may differ from the official recommendations we make in our subscription services such as Share Advisor, Hidden Winners and Pro. Here at The Motley Fool we believe that considering a diverse range of insights makes us better investors.

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