In the first screenshot I can't tell if that's from a trunking personality or conventional personality, if it's conventional and you're wanting the talk permit tone it has to be on a P25 repeater with very specific repeater side settings for the radio to give you the grant. I have two ham P25 repeaters near me, both quantars, one will give the grant while the other won't
If it's trunking and you're not getting the tone the only thing I can think of is the mute setting you have for tones, but it looks like in the second screenshot you just have it set to keypad tones so you should still hear the talk permit tone
If you can provide us more details on the system you're trying to program, preferably a link to it in the database we may be able to provide more insight