Please do take ure kitty in asap.
Keep in mind that him peeing elsewhere may be because he is in pain from his anal glands (u said they looked like they may have ruptured again) and he is now associating pain with the litter box and hence is doing his business elsewhere.
When cats have a urine tract infection one of the first signs may be that they will pee outside the litterbox and this is because they associate pain when peeing with the litterbox.
If everything else checks out fine it may just be that pain association with his anal glands.
regarding the anal glands, does he scoot often? What do you feed him? My cat Onnie has had recurrent anal gland issues in the past when he needed to get them expressed. Luckily, we took him in before they ruptured as my brother was watching him one day as he begad to scoot.
What helped for us was to change his food as well as supplement with baby food squash (for the fibre, it adds more bulk to the stool allowing the glands to be squeezed naturally). Since then no issues
* Thanks growler and sugarcatmom*