The best way to do this would be to create a copy of the label Step Type and change that copied data type to automatically record results. To do this, go to the Types Window (Ctrl+T), then go to NI_Types.ini. From here, copy the label Step Type (just right click and copy). Now go to MyTypes.ini (in the same Types Window) and paste the step twice (the first paste just copies a reference, to create a new one you'll want to paste the second time). You can delete the first one (don't delete the EditSubstep) and now you have your second one to work with.
Name it whatever you like (can't be the same name as Label) and then Right-Click, go to Properties. Now go to the Default Run Options tab and check the Record Results box. Also, you can change the menu item to be named something different (like Label with Record Results or something). Now you can even hide the other label step by right-clicking the insertion palette and going to customize and then hiding the Label step type. If you need the step type on multiple machines, just copy the MyTypes.ini file to <TESTSTAND>\Components\User\TypePalettes where <TESTSTAND> is your installed TestStand directory (this is also where it is located on your machine). Doing all of this should give you everything you need and from now on you'll just use your new custom step type instead of the old NI one.