http://arachnoid.com/equities_myths
Warren Buffet has chosen index funds as the basic approach for his estate and relatives after he's gone.
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/...
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.
I use the simple strategy of (1 - my_age)% in the stock market and the rest in fixed income funds(or less risky investments, including some hedge in gold and dolar due the fact that I live in the third world and currency fluctuations happen frequently).
It's funny because even though I work with software development, I don't have much interest about internet companies(read FB, TW and so on). The other sectors in the industry are less of a gamble and I like that.
25% in Vanguard dividend growth index fund
25% in Vanguard total stock market index fund
25% in Vanguard total bond market index fund
25% in stocks I chose myself
now i just buy aaa bonds and sp500. lost too much gamblin' alreafy.