male cat peeing on items

Question
Hi, First I would like to thank you for reading this, I have a question about my cat. His name is boo, He is 1 1/2 years old right now, he is a very fun, and funny cat. He is more like a dog, comes to the door to greet people, likes to play fatch, like to steal people food, can be a trouble maker, he has a older cat sister who is nothing like him, you do not see her until night time, he truely enjoys tackling her, and chasing her, she will play for a while and then runs away. My problem with boo started at about 4 months old, he started peeing on our clothes, but only in baskets, and he likes them to be clean. He had a bad case of worms and bloody stools for about 6 months, he was going to the vet about 1 time every 2 weeks, we had to what to fix him until 7 months, at that time the vet felt he was health enough to be fixed, after that the spraying only got worse and it gets worse everyday, i have spent hundreds of dollars on getting him checked out blood test from kitty aids to white blood cell counts everything was ok. I have had his urine check, anything i can think. we truely love him, but he is ruining are things, 5 months ago he started pooping and peeing behind a cabinet in the basement, i could not find the smell until on day i went downstairs to get something and the wall caved-in from all the poop and pee, we had to knock it down, has an electirican come in and redo the curcuit box and all of the board that it hung on had to be removed and replaced, next my kids beds, and my bed only pee this time, the clothes anytime he can and now he has upgraded to going in the drawers if the kid leave them open, and he now feels the need to go in the kids toys, he has destroyed there bean bag chairs, not anyother furnitre thank god!!!!! I know there are somethings that he wants that I just can not let him do, first he wants outside, I live in a city not large but not safe for him to go out, she chewed through a screen this summer and I did not know he did this I looked out side and he was laying in the street, just catching a tan, I can not have windows open because he eat the screens to get out, I also live by a river and the eagles would love him for a snack, and he is declawed.  Next he wants in the attack which we just had work done on and he got in, they had put a hole in the wall and he found it, there is espestis in the attack and it would be far to dangrus to him and to the kids do to the fact that he would has it on his fur, no he will sit and cry at the spot the whole was in.  I have tried changing his diet, we have 5 litter boxes with 5 different litters in it to see if there is one he likes the best, no we each have a litter box in our rooms one in the kitchen one in the bathroom one in the living room one in the basement and one in the kids play room, he is normally very busy as I said before but then he will get very lazy, and sleep for days, and he eats non-stop, and becomes very upset when I try to limit his food. I can not have him keep ruining thing in my house, the lates, all of the chirstmas thing were peed on, when we took them out, the vet said that he probably will not stop and that no one wants a cat that pees on things so the only option are 1 take him to a farm- he has no claws I do not think he would make it, also love people far to much for that, 2- medicate him which we can not aford the price of it for a short while yes but long term i just do not think so vet said it most likly will not work, 3 and the worst put him to sleep, it makes me sick to think about that, I have tried products over the counter for cats felway I think that is how you spell it but did not help, and he never pees in the same spot and never when we are around, I cought him by chance a couple of times, I do not know what to do, please help He is part of my family, and I love him. But I just cant take it and the smell is so bad. I use so much vingar in my house each day to try to get ride of the smell that you would think you entered a pickel factory. but it is better then the smell of his spray

Answer
Tiffany,

Here are some things to read: (copy and paste or type the WHOLE link into your address bar)

http://www.geocities.com/heartland/pointe/9352/litterboxhelp.html

http://cats.about.com/cs/cleaningmesses/a/cleaningmesses.htm

http://cats.about.com/cs/behavioralissues/a/outsidebox_two.htm

These articles are excellent in explaining some cures for your litterbox problem cat. I know it's miserable, especially if it's a nice cat.

I know it's not safe, but if he is doing it because he is so upset at not being able to go out, you may want to let him go outside, if for nothing else to save your house. Collar train him and tape your name and address on it in case he wanders and someone thinks he is a stray.

You can also leash train him and take him outside. Here is how to do it:

http://www.hdw-inc.com/leashtraining.htm

I hope this helps!

Tabbi