We have an older cat - he's about 13-14 now. He's always had a slight health issue where he would occasionally get constipated to the point of it being painful and him throwing up a lot - it would fix itself and life would go on. We were given the choice of living with it or having surgery and given he was a feral cat that didn't exactly take to the vet we just dealt with it and the cleanup. Recently, however, his health has taken a bad turn.
First, he had a flea problem last year (he's an indoor cat - one of us must have brought them into the house) - he licked himself alot and as a result is fairly bald from his mid section back - the fur just never grew back the same. It's only looks - but my worry is the lack of hair is a pretty good sign he's getting old - I think in his youth it probably would have grown back. Additionally, he's lost a lot of weight visibly. He also has always been, let's say amorous, towards our other (male) cat - but only on occasion. Lately it's been just about every night that he's tried climbing on top and howling/meowing loudly and it's obviously not something the other cat is fond of as he's getting bitten/attacked in the process.
He's still super loving to my wife and I and our son still but with strangers he can get ugly and growl/hiss and attack (he's always been that way - just worse over the past year or so). But the final straw is that he's taken to using the tile area by our back door as his litter box, despite having a nice clean one available just as they have for 13 years now. He moves a bit more lamely lately, it just looks like often he appears to be in some pain, so I'm discussing with the wife putting a new litter box up to in bathroom (instead of the basement) but I don't even see him try to go down to it, which makes me think it's behavioral.
I guess the tough question is at what point do you decide to let a cat go and have it put down? I know there could be issues we could help treat with vet visits, medication, moving our home around, but in terms of cost vs benefit he's old - he acts old, looks old, and considering he's always been a feisty bastard, it's not going to really fix that - I feel like we'd be stretching out the inevitable at this point. Is it wrong to be thinking that for a wild cat he had a very good life and that the combination of health and behavior might be too much at this point?
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My take is that as a pet owner, your responsibility is to provide as good a life as you can for as long as you can. If caring for your cat is becoming too burdensome, and you can't reasonably find him a new home (as you say, he's old and unfriendly, and moving him to a new family would probably be traumatic for him anyway), then you're not wrong to put him down. It does sound like he's had a good life, so you have nothing to feel guilty about.
It may also be that this is the beginning of the final decline for him, and you may be sparing him a long, slow death by ending it now. Cats aren't human; they don't have an existential fear of death the way we do. It's kinder not to let them suffer.
You have to decide at what point for yourself is the right time to put the cat to sleep. This is more for you than it is for the cat. For me, this past year we lost our dear little Mollie. She was an older cat, but she had stopped eating anything, even her favorite foods. We took her to the vet, and they found a liver mass consistent with a tumor, likely cancer. We did some palliative treatments, and her appetite picked up for a short while, but in the end, when she couldn't eat on her own, that was the point at which we decided it was time.
Honestly, it kills me to even think about this - he was a college graduation gift to my fiancee (now my wife) and despite being a jackass to others he's been an awesome pet for us and I have no idea how I'll tell my son. Part of me knows that for his own good that we should be strongly considering this - but I'm trying to avoid the guilt involved in the actual decision.
Make him comfortable, spoil him, give him tons of attention before you do it -- if that's what you decide. The alternatives are worse.
Putting a litterbox where he's going might be enough for him though, assuming he doesn't just move.
Unless something significantly changes our solution as of last night was I'm removing the door from our bathroom linen closet and putting in a litter box for him. We are going to try that for awhile and make a decision in July. He doesn't seem to be in pain except for his unwillingness to climb downstairs - he's still super affectionate to us, and still jumps up and climbs all over us. I actually carried him down to the litter box last night and this morning and aside from him be ticked at me during the carrying, he immediately used the box and walked back upstairs just fine - slightly slow, but nothing horrible.
Of course if he goes down hill we'll have to rethink our plan, but I don't want to have him put to sleep if his behavior is all a result of his litter box being hard for him to get down to.