Come to think of it, the Cloak probably not. The life forms that disintegrate on Titan do so one at a time, but the cloak disintegrates at the same time as Strange, as if it’s just another part of his clothes.
If the Iron Spider suit has an AI, the same argument applies there.
That strikes me as a fairly cheap argument. Like saying Vision isn't worthy because an elevator could lift Thor's hammer.
It's abundantly clear that forms do not have to disintegrate one at a time, because if they did it would take days or weeks or even months for a large city to be fully effected. Not to mention that A4 is apparently explicitly saying the snap affected animal life, too, so the same issue would apply to almost anywhere on earth where insects live.
And that's without even going into the question of whether being 'alive' for the purposes of the snap has any real relationship at all to being in any way 'sentient'. Thanos may have easily killed half the bugs in the universe but not killed a single robot, regardless of sentience. Robots in sci-fi typically don't use up resources like biological life forms, so could logically be exempt to begin with. The cloak and the ai's would fall under the same category, except they have the misfortune of being attached to a biological lifeform who takes them with them.
As for the rest of the discussion, I really never got the impression at all that Jarvis had no free will or that he never 'existed' for himself except when Tony gave him something to do, but in order to really try to gather the evidence for that, I'd have to hold a major rewatch which I don't have time for right now. So I'll just say that, in general, Jarvis seems extremely similar to Vision in almost every way. In fact the only undisputable difference I see is that Vision falls in love and Jarvis doesn't, but that could simply be a question of opportunity. Certainly Jarvis seemed to take the initiative quite often, including in AoU when he actively opposed Ultron without any instruction from Stark, even after his programming had been 'destroyed'.
Friday and Karen appear much more superficial, and maybe they are, but maybe that's just a function of their limited screen time. Either way, the key to the discussion is obviously Jarvis. If he could be considered sentient, then all Stark AI's would either be sentient or at least have the potential to develop sentience (possibly, Jarvis 'grew' over time since he was in use for so long - like the Doctor on Voyager).