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reinvest dividends or not?
When I was just starting out, and my portfolio was relatively small, I just reinvested all dividends back into the companies that paid them. This was simplest, and made sense to me as the best way to build momentum -- that is, to grow the size of the snowball as it started rolling downhill. When you're only collecting a hundred or three dollars in dividends each month, it would take forever to pool them up to make a separate purchase. I understand that this may not be optimal in terms of entry prices at the time each dividend is paid, but it was simple, predictable, and helped the portfolio grow visibly quarter after quarter.

Now that my portfolio is larger, however, and throwing out more than a thousand each month in dividends, I generally pool them up and make separate new purchases with the proceeds. When a company that I like a lot is trading in a good price range, I sometimes just click the "automatic reinvest" box (I was doing that with T for a while a year or two ago, and am doing it with MO and PM now), but mostly I let the dividends pile up and reinvest opportunistically.

I've never been a believer in the "ex-div drop," and have never factored it into my decision-making.
I always DRIP. When it's at high prices, I consider it adding to my winners.
I currently DRIP 100%.

But, my "dividend" portfolio is newer, smaller, and split up between 4 different accounts. This makes it hard to generate a notable about of purchasing power each month. In particular, in IRAs, the cash would sit there for several months. I might as well DRIP and let it compound.

I do allocate a portion of my portfolio into high yield, income oriented CEFs. Right now these are set to DRIP, but next year, after more cash contributions, I'm hoping to collect these dividends and include them in my monthly investing.

Thank you,
It depends, I have dripped in retirement accounts and still do in my kplan. In the kplan I automatically reinvest all dividends and capital payout gains because the options are few and far in-between, some are simply just not allowed, for instance, the mutual fund dividends and short/long term gains there is no option to receive those payouts into my kplan's MMA--it simply is not offered as an option. But, a lot of times in the kplan I build up my MMA and purchase shares/units after the dividends/gains are paid out in that particular fund.

In one IRA account, there's only two dividend paying stocks so to make it easy those are re-invested. Set on auto-pilot is easy and it still keeps the snowball rolling. As Kerim stated collecting a few hundred dollars to even a little over a 1k a year in dividends just doesn't make enough sense to collect the cash.

The other IRA and ROTH are all collected in cash and reinvested once a month in what I feel is a quality company at a reasonable price. If there's a recession I may or may not throw it on auto-pilot.

The brokerage account is always collected in cash due to taxes in case I do sell something--I don't want to deal with multiple purchase prices if and or when I do decide to sell something.

So, for me...the answer is

It depends.
Well with E*TRADE slashing their trading costs to $0, one of my main reasons for DRIPing has been eliminated. I turned off the DRIP for all my stocks. Now I will buy stocks (even if it's just one share) when I have money in my account.

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