One generally accepted investing adage is that you "make money on the buy". Meaning, what you pay for an asset will largely determine your fate. Price matters a lot. Some/many would even argue that it's the single most important thing when it comes to investing.

Said differently, if you had to choose between paying above market for a high-quality real estate asset or paying below market for a low-quality real estate asset, you would choose the latter, because you have a higher probability of doing well.

In some ways, I agree with this. If you're buying an asset below what it's actually worth, then in theory you could turn around and sell it tomorrow for the market price. So you are quite literally "making money on the buy."

On the other hand, if you've paid above market for even a high-quality asset, you've now just lost money (at least in the immediate term). Because if you also turned around and sold it tomorrow, you'd lose money.

But is this always the right way to think about investing? One of Warren Buffett's many famous lines is that he'd rather buy a wonderful company at a fair price, than a fair company at a wonderful price.

And this would suggest that "cheap" isn't the only metric to consider. Especially if you think like Buffett does and you want to hold assets forever and benefit from the compound growth that comes along with wonderful assets.

So as obvious as it may seem, a better way to think about "making money on the buy" might be that you need to consider both price and the quality of the asset. Cheap could be a feature, or it could not be. But cheap and wonderful are generally always a good thing.

Perhaps the greatest lesson from Warren Buffet's most recent letter to Berkshire shareholders is that, to be wildly successful, you only have to be right sometimes:

In 58 years of Berkshire management, most of my capital-allocation decisions have been no better than so-so. In some cases, also, bad moves by me have been rescued by very large doses of luck.

Our satisfactory results have been the product of about a dozen truly good decisions – that would be about one every five years – and a sometimes-forgotten advantage that favors long-term investors such as Berkshire.

The lesson for investors: The weeds wither away in significance as the flowers bloom. Over time, it takes just a few winners to work wonders. And, yes, it helps to start early and live into your 90s as well.

So-so decisions. Periodic moments of brilliance. And a long-term patient outlook. These are, I think, important things to keep in mind. It's okay to make mistakes; you just have to keep going.

I have a great deal of respect for Warren Buffet. Much of what I know (or think I know) about investing has come from listening to and watching him and his partner Charlie Munger. Surely they have got to be the most successful investors living today.

But there are some things that I don't always agree with them on. The first and most obvious one is crypto. Warren thinks it is speculative rat poison and I think it is the future of the internet. I understand where he is coming from in that it does not produce cash in the same way as say a farm or an apartment building. But that doesn't mean it won't have value.

The second one, as I have learned today, is maybe streetcars. As a rule, Warren doesn't typically engage in local politics. But he recently decided to break that rule through a letter he wrote to the editor of the Omaha World-Herald, lobbying against a new $306 million project that I believe is going ahead regardless.

Here's an excerpt from the letter:

“Residents can be far better served by extended or more intensive service by the bus system,” Buffett wrote. “As population, commerce and desired destinations shift, a bus system can be re-engineered. Streetcars keep mindlessly rolling on, fuelled by large public subsidies. Mistakes are literally cast in cement.”

I should, however, be clear that (1) I know nothing about Omaha and this streetcar project, and (2) "streetcars" can be nuanced. There are streetcars that compete with car traffic and have short station spacing, and there is light rail transit on its own dedicated tracks and with farther station spacing. One size does not fit all.

Here in Toronto, we have lots of the former and they generally move you around at the slowest possible speeds. Sometimes it is faster to just walk. But we are also getting a new light rail line next year and that should move much faster. I can also tell you that when I worked in Dublin many years ago, I took their Luas to the office every day and loved it.

Again, I don't know the specifics of Omaha's streetcar project. Maybe Warren is right or maybe he is wrong. And that's why I was careful to say "maybe" above. But I do know that in the right urban contexts and when done well, I am a fan of light rail transit.