Understanding Gain/Loss

The ROI column isn't always going to produce the value OP is looking for because it doesn't transfer between accounts. I recently transferred an IRA from one firm to another and started a new Quicken account for the new IRA, and when I look at the ROI for the investments in that IRA it only includes the changes in value since the account was transferred, even for investments that were transferred in-kind and were not sold & repurchased. One of the investments in that IRA is currently showing a slightly negative ROI, but my cost basis in that investment is much lower than the current value so it's actually had a gain rather than a loss, but since the gains all occurred while the IRA was at the old firm they aren't included. I can go back and look at the portfolio in the old account right before the transfer happened & see the ROI as of the transfer date but I don't think I can get Quicken to combine those figures & give me the total ROI.

I suppose I could have avoided that by keeping the same Quicken account instead of starting a new one when I moved the IRA but I've never done things that way, I've always kept a 1-1 correlation between Quicken accounts and real world accounts.

Never mind, you can see the total ROI if you look at the investment on the Investing Group and sort the Performance page "By Security".

@jacobs I did use Transfer Shares to move assets to the new account. But if you're looking at the performance page for the individual account I don;t think it's unreasonable for it to show the performance for just that account. When I switch to the Investing Group and look at performance there it seems to include the history of both accounts.

OTOH, the "ROI (%)" column is not giving me the same value as "Market Value/CostBasis - 1" so I'm still not fully confidant in that number.

But my confusion comes with reinvested dividends (all my dividends are reinvested)

In my example, with the dividend paid in cash, the math was simple: "what you made" was the gain on the initial investment ($300) plus the dividend paid in cash ($200) = $500 or a 50% ROI.

If the dividend is reinvested, calculating the ROI is trickier, because now the dividend reinvested in additional shares is also gaining value. It's the same as compounding interest. So your ROI should now be higher than 50% because instead of your dividend sitting idle as cash, it purchased additional shares which have experienced their own gain.

So in my example above, if I change the 6/30/24 Dividend transaction to a Reinvest Dividend transaction, with the $200 dividend purchasing 20 additional shares at $10 on that date, then the ROI goes up to 56%. That's because the security is now worth $13 per share, so your $200 reinvested dividends have grown from $10 to $13 per share and now have a value of $260.

(In real life, your reinvested dividend would have been bought at a different price than your original investment, but I kept the price at $10/share for illustration just to make the math clearer.)

So what is the ROI? ROI is calculated by subtracting the initial cost of the investment from its final value, then dividing this new number by the cost of the investment, and multiplying it by 100. So in this case: $1,560 - $1,000 = $560 ÷ $1,000 x 100 = 56%.

So going all the way back to your original "what did I make on this investment", it's simply market value minus your original investment (not counting reinvestments): $1,560 - $1,000 = $560. Quicken doesn't show you your original purchase amount for a security, because for most purposes, you're concerned with your cost basis, not the original purchase amount. So I think you'll need to do this calculation manually if this is the number you want to know. (If someone else knows a way to show that value, hopefully they'll jump in here.)

@Steve29 I understand what you're looking for. What you should do is create an Idea post; Ideas are requests for new features or functionality in the program. Navigate to Product Ideas > Ideas for Mac Classic > Investments. Idea threads are open for other users to add their votes if they agree it would be a useful feature, and to add their own comments; the developers particularly welcome use cases that illustrate how/why a feature would be useful. When Idea topics reach a necessary threshold of votes, they are forwarded to the development team for consideration of usefulness, work involved in possible implementation, and where it fits in context with all their other priorities.

It's best to keep each Idea post focused on one issue; that makes it feasible for other users to add their votes and comments, and for the developers to grasp what's being asked for.

But before you create a new topic, you should review a few of the existing Idea topics in that section which, I believe, hit on some of the things you're asking for. In particular, I think this addresses your first bullet point — and the good news is that the developers have marked it as "Planned" for future development.

Click on any/all of these View Post links to add you vote and, optionally, comments to the topics. More votes get these ideas closer to being considered by the developers for their future schedule.

@Steve29 It's not a matter of what's "debatable" or not, nor what's "simple" or "basic". And I definitely don't think it's rooted in management believing that Quicken Mac users aren't serious investors.

(If I had a quarter for every time some user has said that a feature is "simple"/"basic"/"obvious" or something which could be done in "an evening of work" or something which a "high school student could do" or that the developers are "brain dead" or "don't care about users", I think I'd have enough money by now to have someone manage my personal finances for me instead of using Quicken! 🤣🤣)

The issue is simply that there are hundreds of feature requests, some small and some large, and the small Mac development team can only churn out a few things every other month or so. If they prioritize the smaller things that some people want, then some of the big development projects never get going; if they tackle big projects which consume multiple members of the development team for many months, then relatively few smaller things get worked on — so they're damned if they do and damned if they don't. How they actually decide which things to work on and which to let wait for a while longer is something we're never privy to.

And you're right that the investment area of the program hasn't received a lot of attention over the years. Recently, we're starting to see new investment features being rolled out, such as the Watchlist and Security Details screens. you might feel those aren't as useful as other investment features, but they are things users have asked for over the years. And often what gets developed when depends on who on the development team is needed to implement particular features. My hope is that there will be a time when some major investment requests, particularly in the area of reporting, get tackled. Right now, the things the developers have teed up (e.g. marked as "Planned") seem to be largely focused on planning functionality: revamping the budget, adding planners for debt reduction, savings, and taxes, etc., as well as rounding out key core features of the business section of the program they debuted close to a year ago. So I'm not expecting to see major investment feature changes in the short-term future, but maybe we'll be pleasantly surprised.