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How to find "original" principal invested (ignoring rolling amounts due to gains from original investment in subsequent investments) ?

I have a very important question which I could not figure out how Quicken can help answer regarding my investments.  I will appreciate if someone can provide the answer / point to the right resource for same.

I need to find out as to How much of my own money (principal if I can use that word) is invested into my portfolio ? It appeared very simple initially as the Net amount invested report gives the same but here is the catch. I need only my "original principal" and not the net amount invested across all the stocks / mutual funds (i.e. bought - sold). This is because I might have purchased first stock, made a gain out of the same by selling it partially and bought second stock from the gains of the first stock. Hence, the amount invested in the second stock does not really come from my original principal but rather gains from the first stock. Now, I will have two stocks in the portfolio and the above scenario will repeat itself tens of times over the years as the stocks will keep on rolling through buys and sells. Hence, it becomes very difficult to find the original sum invested. At the end, if this sum is positive, that means my money is in stocks and if this sum is negative, it means that I have recovered all my principal and my stock holdings is entirely from the returns from the market or dividend income etc.

I also understand that as per IRS, the cost basis of each stock has to be separately calculated. However, I do not want the above mentioned report for tax purposes. It is only for my understanding of amounts invested irrespective of  tax laws.
    Quicken has no way of knowing what stocks were purchased with capital gains and which were purchased with out of pocket investment capital.  This is an exercise you will have to do by hand.
    • I thank DaveT for the update.

      With the assumption that ALL my investments are entered in Quicken and available there across all the dates from beginning until now, I presume that all my capital gains, subsequent investments etc. will be available in Quicken.

       I will appreciate if some "manual" way of how this can be done "by hand" can be elaborated. I am sure that there should exist some way which would involve existing Quicken transactions, reports along with exporting the same to Excel and doing some more analysis there to get the "out of pocket" investment.

      This answer will also be immensely useful to many readers, I guess as finally we all wish to live off the "returns" and recovering the "principal" and this answers the same to an extent by letting us know how much "principal" has to be recovered.
    I cannot imagine a way to truly come up with a meaningful answer to your scenario nor do I see any practical value for that perspective, though I can see how it sounds attractive on the surface.  Let me add the other complication into where you started - taxes.  

    You bought $100 of stock, sold half that holding for $75 returning $50 in 'principal' and $25 in gains.  You then bought a second stock with the $75.  You seem to want to say the 'principal' in the now two holdings is still $100 - $50 in each stock.  But in reality you paid (let's say) $5 in taxes on that capital gain from you other assets.  I would then suggest that the $5 you chose not to withdraw from the account to pay the Cap Gains tax represents another $5 you contributed to the investment principal; thus your total principal might now be identified as $105.  It is a matter of how you choose to view your data.  

    Another problematic scenario - Mergers and spinoffs.  Suppose you started with $100 "principal" in Ma Bell before the breakup.  That became perhaps $7 in each of the seven Baby Bells + $51 still in Ma Bell.  But then they began swallowing up each other and generating other spinoffs until SBC got big enought to gulp down Ma Bell and regenerate into the new ATT.  There is no way I can imagine in Quicken to report on the data you want from that type of history.  

    About all I can imagine you doing is tracking how much cash you have added into the account(s) over the years.  But what about the withdrawal?  Were they from cap gains to pay taxes, from div and interest to pay taxes, from "principal"?  Generally, I don't see that it matters.  A dollar withdrawn is a dollar withdawn regardless of how it got created.  

    If your accounts of interest are simple enough (a straight through 401k or IRA without rollovers) with only cash deposits, you should be able to determine what you contributed by selectively customizing woth Actions.  For most real-world accounts, I would categorize your potential efforts as futile and excessively frustrating.

    • I wish to thank q.lurker for detailed explanation.

      I understand from the explanation that it will be very difficult if not impossible and also very frustrating if taxes, corporate actions etc. get into the picture which will always happen in real world. (I myself had great difficulty when mergers and acquisitions took place where old stock's conversion happened where part was paid in cash and part in stock of new company even for performance calculation of the original stock and even now cannot understand it fully).

      My only wish was finding out total "out of pocket" expenses to the extent possible balancing it with simplicity at the same time.
      e.g. If I take the example provided by q.lurker,

      I was thinking on lines of

      If I buy a stock worth $100
      Sell half of that for $75 (so $50 principal and $25 capital gains)
      Then I buy another stock with $75

      As q.lurker mentions, if I do not take taxes into account, my principal is still $100

      If the company later splits into multiple companies or merger or acquisition occurs, I get few shares in each company. However, as I have not paid "out of pocket" for any of this shares, my principal is still $100.
      Only when I buy some more shares from one of the split companies or a new company (where the total cost basis of new stock exceeds my realized gains and income (in Quicken terms) from old stock with "new" money from "pocket", will it get added to the principal or out of pocket amount (which will essentially be difference between (new stock total cost basis) - (realized capital gains + dividend income from old stock).

      I am not sure if by exporting all the transactions to an Excel and then sorting it by date, buy/sell/dividend income/corporate action  and transaction amount and calculating a "running" total "somehow by adding the buy amounts, subtracting the (sells, capital gains and dividends)" for each row of the above sorted Excel might help (at least in simple situations without taking taxes and mergers / acquistions into account).

      It will be very helpful if something like above can be suggested / referred in more detail which is workable  and can be accomplished by taking Quicken transactions/reports and using Excel for further calculations. This is because what I have mentioned above regarding Excel is only "idea" that comes to my mind and not "real world" implementation of same has been done yet.

      Thanking in advance,

    OK, because you insist in spite of q.lurker's feedback, here is an approach you can try.

    This method depends upon having all your investment activity captured in Quicken from the date of your first investment purchase.  

    Further assumptions, (1) all dividends, interest, and capital gains distributions were reinvested, (2) all realized capital gains were reinvested, and, (3) any income tax liabilities were absorbed personally and not paid from investment income.  

    If all your investment activity was entered into Quicken since the inception of your investment account, then use Quicken reports to generate an Investment Income report.

    Click Investing > Reports > Investment Income, then change the date range to "Earliest to Date".  

    The report should list the amount of your dividend and interest income, long and short term capital gain distributions, and your realized gains.  Adding these amounts and subtracting that total from your porfolio's cost basis (from account overview) should come close to the amount of your out of pocket investment capital without regard to income tax consequences
    To see if you can live off the "returns" and to see whether you will outlive your principal, suggest you use the Retirement Planner in Quicken which will take into account a lot of lifestyle income and expenses in addition to your investment balances to give you an estimate of your ability to "retire" on your investments.

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