I am using Money Plus. If you are using an older version, some thing may differ.
If you did not do so, you can enable the Capital Gains shortcut by clicking Shortcuts [K].
Click the Capital Gains shortcut [A], or alternatively InvestingTools->CapitalGainsEstimator [J].
EstimateCapitalGainsTax [B] in the left column. There will be some delay for the table to be prepared.
The Sale Price column [C] will have numbers in it. I found that the numbers were stale. I wanted this column to reflect the latest price info that Money knows. To trigger that, click UpdatePrices->UpdatePricesManually[D]. The clicking either then X or Close caused my numbers to update. Unfortunately this table cannot be sorted.
See the Unrealized Gain column [E]. Those with a parenthesis around the number are candidates for sale. But there could be others. The Cost Basis column [G] may have "multiple lots" listed for some securities. If for those you click the + sign to the left, a - sign appears, and the lots will be shown [H]. For a stock in the US, you can identify specific lots for your sale. The method for doing that varies with your broker.
So take notes, and enter your orders with your broker. In this example, you might enter an order to sell the 100 Kirby (KEX) shares bought 6/12/2018 and keep the earlier 200 shares.
If you want to buy the same stock back later, and still take your tax loss, you will have to do the buy 31 days or more later.