Best way to track stocks, securities, and dividends?

Greetings,

Could someone kindly provide a link—or perhaps just offer a brief explanation—regarding how businesses (though this certainly applies to individuals as well) should manage the bookkeeping for assets held in stocks and other securities; specifically, assets with a "transparent" market value, such as corporate bonds, fund shares, or precious metals? Furthermore, I am curious about how one accounts for paid dividends and similar premiums within those records. Please bear with me regarding my terminology, as I do not come from a formal financial background. My central question concerns the calculation of ROI for a capital investment when one must factor in dividends over a multi-year period.

To provide a simple illustration so you might grasp the scope of my inquiry:

2012:

On June 1, 2012, a company purchases 1,000 shares of Apple Inc. at a value of $0.00, ($0.33 per share).

By December 31, 2012—the final day of that year—the firm still holds all 1,000 shares, but their total value sits at $317 because the share price has dropped to $317.

Moving into 2013:

On March 30, 2013, the market price for a single share is $267. The company sells 600 of those shares (at $160 each), leaving them with 400 shares valued at $107.

In practical terms, the company has effectively lost $67 since the inception of the investment. This part may seem straightforward, but I am struggling with the accounting aspect—specifically, how this is recorded given that the purchase occurred in 2012, a portion was liquidated in 2013, and the firm remains a partial owner. The multi-year bookkeeping and the aggregate calculation of profit and loss are what truly trouble me.

The complexity increases significantly if there were intervening transactions or dividend payouts:

On May 5, 2013, while the share price remains at $267, a dividend is issued, and based on the remaining 400 shares, the firm receives $13 (which is $33 per share).
Does this mean the realized loss in this scenario is reduced to $53, or does that amount get categorized under a completely different ledger item?

A few months later, on September 1, 2013, the share price falls to $233 (meaning the firm's asset value is now $233 * 400 shares = $93, not including the dividend received, which is being held as cash in the bank),
and on that very same day, the firm purchases an additional 400 shares for $93, bringing their total holdings to 800 shares valued at $187.

Finally, on December 31, 2013—the end of the fiscal year—one share is worth $300, meaning the firm's total asset value stands at $240 since they own 800 shares.

I am asking for some "newbie" assistance on how this entire saga should be booked, how to calculate the ultimate profit or loss, and how those figures are allocated across the different years...

My apologies if my inquiry lacks clarity.

To begin with, you must first decide how you intend to classify these shares under your financial asset categories (per FASB standards).
Given that we are discussing equities and looking at the nature of these transactions, I suspect we are dealing with financial assets held at fair value through profit or loss.

In practice, when acquiring shares, you should initially record them on a clearing account (an asset in Class 1), representing the transfer from your checking account to your broker or custodian.

Once that is settled, you clear the clearing account (which, by the way, doesn't necessarily have to be a clearing account if you maintain a constant cash deposit in your custodial account for future trades—in which case it functions much like a short-term deposit sitting alongside your Chase or Bank of America accounts).
Essentially, you credit the broker's clearing account to close it out, then debit the acquisition of shares at fair value through profit or loss within Class 1 (short-term financial assets—equities). Brokerage commissions and custodial fees for this specific category (FVTPL) ought to be recorded separately...

At least once a year—typically on December 31st—you must perform a portfolio revaluation based on the closing market price from the final trading day.
Under current U.S. tax law, unrealized gains are recognized for tax purposes, whereas unrealized losses are not; put simply, you end up paying taxes on shares you’ve marked up in value even if you haven't actually sold them at a loss yet...
In the subsequent period, there is an option to adjust for such temporary tax differences.

Dividends are not bundled directly into the portfolio value for this asset class (FVTPL); rather, they should be recorded separately as a receivable for dividends or dividend income—specifically for trading securities.

If you find yourself trading frequently amidst significant market volatility, it might be prudent to apply a weighted average cost method during your portfolio revaluations. It isn't strictly mandatory, of course, but it does provide some measure of clarity...