No, Matt, it won’t help. Your cat is engaging in territorial marking behavior, which is part of a completely different instinctual system than elimination. Although spraying is the most common form of territorial marking, the cat doesn’t have to spray to mark territory. What tipped me off to this is when you said he only partially empties his bladder at various places throughout the apartment. This is what male animals do; it’s why dogs have to stop at every tree and deposit urine when they’re out for walks.
Your clothes and your bed have your scent on them most strongly. That’s why he chooses them for targets; he’s superimposing his scent over yours. This is also natural instinctive behavior. In the wild, animals will put their own scent on top of a place where they smell another animal’s scent. Sometimes they even establish a “community marking post,” a particular tree or something where everyone marks just to let others know they’re around.
Having the cat neutered at 9 months used to be recommended procedure, but it no longer is. Veterinary research has found that the concerns once voiced about the male’s urinary system not developing properly if neutering took place earlier do not happen. Shelter kittens are given what is called a pediatric neuter (or spay) as soon as they attain a certain weight. I think they hit that weight around 2 or 3 months of age. If this behavior became established before the cat was neutered, I’m afraid it’s going to be difficult to stop it. Once those hormones kick in and the instinctive sex-linked behaviors start, it can take a long time for them to go away even after neutering.
So you see, Matt, from your cat’s perspective, this isn’t a behavior problem; it’s what his instincts tell him he’s supposed to do. You can’t change that behavior through punishment of any kind. I recommend you talk with your vet about this. Make it clear that you’re dealing with territorial marking and ask for advice about that. I hope you can find an answer to this problem.