
Recently I was privileged to work with a client whose income came half from real estate rentals and half from stock market investing. After a series of QuickBooks accountants and bookkeepers had messed up his bookkeeping, it was like a tangled mess of hair. Different people had tried this and that way of tracking his stock market investments, none of which were successful.

What tax preparers want to know is date of purchase, # of
shares purchased, total cost, minus any brokerage fees. Even if you hold that
stock for years, decades, you still need this information when you sell for tax
purposes. Make a file for "stock purchases" to store the paper that
outlines the trade there. One advantage of Quicken is that if the stock pays dividends
and interest, you can see watch how profitable this stock is for you.
If I had to track stock market investments in QuickBooks, I would
use items and track it the way one tracks job costing. Each stock would be an
item, with additional items for brokerage fees, etc. The purchase would be
tracked as a purchase order, and the sale as a sales receipt or
invoice/payment. There is a job costing report to show profit. But once again I
recommend Quicken for tracking your stock portfolio.