I’m eyeing up some Stocks and Shares ISA investments over the winter, and my money will be mostly going into dividend shares.

My big problem is that there are so many attractive yields out there, it’s hard to choose.

If I had the cash ready today, a portion of it would almost certainly go into savings and investments manager M&G (LSE: MNG).

The M&G share price has been flat for the past few years, and that’s helped push the forecast dividend yield as high as 9.5%.

No free money

There’s no such thing as risk-free cash, and we can never guaranteed a dividend. Sometimes, the earnings just aren’t there to cover it… which is exactly what happened to M&G in the last two years.

It still kept up the payments, though. And forecasts show the dividends should be covered by earnings in the next few years. But only just.

If they’re right, earnings per share (EPS) should bounce back this year, but then stay largely flat for the next two years. And EPS would cover the forecast dividends by only around 1.2 to 1.3 times.

So the dividend could come under pressure, and the shares could tank if we have a cut.

But the key reason I want to buy is that I think the UK stock market could be in for a long bull run. And if it is, investment managers should do well.

Torn

The next FTSE 100 dividend that I really like the look of leaves me torn, for ethical reasons. It’s British American Tobacco (LSE: BATS).

Despite a strong share price run this year, forecasts still put the dividend yield up at 8.5%.

Clearly, the future of tobacco defines the real long-term risk. And I do think that smoking the stuff will eventually die out.

I reckon it could take a very long time to convince the billions in the developing world to kick the habit, though. And British American is leading the way with alternative ways of consuming it.

There’s a fair bit of guesswork on my part there, though. And we really don’t know what kind of market those vape things will eventually enjoy.

I probably won’t buy, simply because it’s tobacco. But I wish I could feel comfortable going for that fat dividend.

Buy the grid

I really should buy some National Grid (LSE: NG.), with its 5.5% forecast yield. I’ve been telling myself that for years, but I’ve never actually hit the button.

I’m not really sure why, but it’s probably down to something else catching my eye each time I have the money. A bigger yield, maybe a growth stock, or a super cheap small cap.

Whatever it is, I’ve missed out on decades of what I reckon has turned out to be one of the Footsie’s best dividend stocks.

This year’s new equity issue, which has diluted the dividend a bit, shook confidence in National Grid. And having done it, will the company need to find more cash for expansion again?

That’s possible, and it could keep sentiment weak. But I must buy some one day.