I am populating my military aircraft experience in airlineapps.com and am not certain how to answer a few of the qustions.
"Requires type rating" and
"Typed in this A/C (PIC only)"
I'm tracking that FAA requires a type rating for aircraft over 12,500 lbs or turbojet-powered, regardless of weight. Having never approached the FAA to have military aircraft added to my commercial certificate, it's not clear to me whether I should indicate yes to both with valid USAF Form 8 checkrides (or whether it even matters since the type of flying is military, Part 121.436(c). Thoughts? Apologies if this is already discussed elsewhere or blatantly obvious.

I don't know if it's the "correct" answer but I entered yes for anything requiring a inst/qual checkride (ie. every military aircraft).

I suggest researching resume/app review and interview prep services and have them take a look at your app. They will have better answers than you'll find on the forums and the money spent on app review and interview prep is worth it in my opinion.

What exactly is the question they are asking? The FAR you mentioned is for applying military experience towards being PIC in a part 135 operation (if I read it right).

Your military colleagues will chime in—but a more clear example of your application question is useful.

I'm pretty sure those refer to FAA type ratings only. Which might apply if you got issued an actual FAA type for something like a C-40 or P-8.

But as was suggested, check with a prep or app review service.

Thanks for responding. Airlineapps simply lists the two with a check box (i.e., yes or no). So it is asking "requires type rating: yes or no" and "typed in this A/C (PIC only): yes or no". Hence, the confusion when applied to military aircraft.

What MWS are you coming from? Some you can get a FAA type rating for by showing your local FSDO your form 8. Bombers, fighters, and maybe a few other things probably won’t have a type rating with the FAA. In any case, you should max out everything you can get from the FAA by simply showing them your FEF and flight records. Extra type ratings are extra points on your applications. Granted, it’s a pilot’s job market right now, but don’t unnecessarily be caught flat footed if things change.