[OGiR]

I personally own (not through a broker) shares in a diversified portfolio of companies, all of which offer Dividend Reinvestment Plans with optional cash purchases of additional shares directly through the company's transfer agent. This means that I pay no fees when purchasing additional shares for my DRiPs, in fact, a lot of the companies I invest in offer discounts on shares purchased through their Share Purchase Plan. I mostly invest in large companies that pay reasonable dividends with long histories of stability and dividend payments/increases. My goal is to almost never stop buying, making use of dollar cost averaging, and earn a safe return that ought to still beat the market in order to save for retirement/other future investments.

[PhantomGremlin]

Buying DRIP stock has a lot of tax complexity. You establish a new cost basis for stock with every dividend you receive. I.e. 4x a year.

   Above all, the importance of recordkeeping cannot be
   overstated. Unlike other tax-related documents, DRIP
   statements, recording all reinvestments and OCPs,
   should be kept indefinitely. [1]

But if you die and leave everything to your heirs, all is forgiven. They get a brand new tax basis and it no longer matters when you bought.

[1] https://finance.yahoo.com/education/drip/dspp_plans/article/...

[OGiR]

Thanks for the advice. It is important not to overlook the downsides of any investment strategy, and I do keep very diligent records.

The downside to DRiPs as you mentioned is the amount of paperwork you have to do and the difficulty in selling. For me, however, I am willing to incur that cost for the upsides which are particularly maximized by my personal situation.

I am not sure about how difficult US taxes are, but in Canada they are fairly straightforward for someone adept at math and logic.