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Hello, this is Dr. Jess. I am so sorry to hear about your kitty! Give me a few minutes here and I will type some ideas for you.
As far as the licking under the tail- we can see this with dermatitis and skin irritation, anal gland irriation, but we can see them lick their penis with urinary issues. Has he been urinating normally? Any concerns there? Any accidents outside the litterbox? Is he definitely urinating? We do worry in male cats about urinary blockages, want to be sure he is going potty!
The best thing you can do to get your kitty to become comfortable with the cat carrier would be to start feeding him in it! Food is a great motivator for cats. I would perhaps start with the food next to the carrier but outside of it for several days, until your cat seems ok with this. Then move the food into the front of the carrier, so your kitty has to stick his head into the carrier,but doesn't have to go all the way inside. Once your kitty is comfortable sticking his head into the carrier,then move the food further inside. If you are patient, and your kitty is motivated by food, eventually he should go inside.
A soft sided carrier may be more ideal if it is larger and has a more open feeling.
Another option which may not look fancy is a cardboard box! If it is a sturdy box that can be taped closed and the bottom is securly taped, with some holes poked in the side for air, it will work! Sometimes that may be easier (some cats like to play in cardboard boxes). Vets see pets arrive in all sorts of containers. As long as your cat can breath and it is secure, it is ok!
If you have any other questions, please let me know.. If you do not have any other questions, please take a moment to RATE our conversation so we can know if you were satisfied with your service and I can get credit for helping to answer your question. Thank you and good luck!