How to use Capital Gains Estimator to find investment lots with maximum capital gains

desplin

I would like to find investment lots with the maximum % capital gains. For instance, I want to donate $5000 of stock to a charity and use the most highly appreciated lots available to maximize my tax benefit. I am using the capital gains estimator and have tried telling it to maximize capital gains. It works for a few seconds and comes back with "Quicken found a solution to your goal as described, but it does not meet the accuracy or your requested objectives. Try increasing the time allotted, reducing the accuracy, or adjust the objectives" I have tried adjusting all of these in settings, but keep getting the same error message. Even though it says it found a solution, it won't let me view the results.

Rocket J Squirrel

If you know which stock you want to donate, it may be easier to start a Sell transaction and do Specify Lots and click Maximum Gain. Record the lots and cancel out of the Sell. I never had any luck with Capital Gains Estimator either.

desplin

I have done that in the past. But in this case I don't know which one would be best. I have too many candidates. I was hoping the capital gains estimator would be able to find an optimized solution.

q_lurker

I customize a portfolio view to include the columns among others:

• Cost Basis
• Market Value
• Market Value %
• Gain/Loss, and 
• Gain/Loss % 

Those are all parameters I use in my thought process.
I then sort on the Gain/Loss % column to get the most likely choices to the top.  Those are the ones with the biggest gains as a percentage of their cost basis.  That view may also include multiple accounts and I may group by security (mixing accounts) or by account.

What gets missed in that approach is 'lot' considerations.  I could have an old 'lot' with very big gains (a gifting candidate) but lesser gains in a later lots.  In my case, I don't see that as a big risk. 

I have never found the Cap Gains Estimator very helpful (though the intent is good)..     

desplin

I was primarily interested in the 'lot' considerations. I have many positions that I've held for a long time that have old lots with big gains. I would have thought that the capital gains estimator would have been the ideal tool for that.

I agree--as many times as I've tried to use it, the capital gains estimator has only been a waste of time for me.

> @q_lurker said:
>
> What gets missed in that approach is 'lot' considerations.  I could have an old 'lot' with very big gains (a gifting candidate) but lesser gains in a later lots.  In my case, I don't see that as a big risk. 
>
> I have never found the Cap Gains Estimator very helpful (though the intent is good)..