Ah ha! I see what's going on.
Risky Strike is in the
2018 PDF version of the Elephant in the Room Feat Tax Rules. I was confusing it with the halfling-only feat
Risky Striker, which is melee only (and appears as though it may stack with Power Attack, interestingly).
So the answer to your original question is: no, you're not doing anything wrong. Everything is working as intended, because the Hero Lab files I've written implement the rules described in the
2012 blog post with a couple minor backports from the Yavmir rules that came out before the 2018 PDF.
When the 2018 PDF came out, I took a long hard look at it. When my to-do list hit 60 items, I decided that in the cost/benefit ratio of implementing it, the cost was high and the benefit was low. So I didn't.
As a workaround, I recommend going to the Adjust tab. Under "Other Adjustments", add a copy of "Ranged Damage Bonus", change the drop-down to "untyped bonus", and set the number to whatever you need to add to get your extra 50% for using a two-handed ranged weapon. Use the "Source" and "Duration" fields to make notes to yourself about where this bonus comes from so you'll know what it is.
You will need to remember to increase it when your BAB goes up. And of course if you decide to attack without using Risky Strike, you will need to turn off both Deadly Aim and this adjustment.