Nighttime behavior problems from male cat

Question
QUESTION: Hi-
I'm writing to you on behalf of a female friend who has been having some behavior problems with one of her two male cats.  Her cat is a 10 year old male short haired named Dakota.  For the past 5 months or so, Dakota has been crying out at the door in the evening for his owner to take him out.  Apparently, Dakota was out quite a bit more in his last residence, but when my friend moved to her current apartment in late 2014, she began keeping him indoors more.  She still does take him out around the complex grounds on a leash during the day, but he is kept inside at night.  The crying to go out goes on for a couple of hours in the early evening, and then stops around 10 pm.  My friend has tried squirting water at Dakota with a water bottle, but that is only a temporary help, as he will soon be back at the door crying to go out again.
After my friend goes to bed, in the middle of the night Dakota will start scratching at a small area rug she has outside of her bedroom.  His scratching is loud enough to wake my friend up.  She thinks that he does this because Dakota wants more food during the night.  Apparently Dakota will pester my friend to give him more food whenever his food bowl is less than half full, and he will do this in the middle of the night to get her to put more food in the bowl.
My friend is losing sleep because of Dakota's behavior problems and doesn't know what to do.  She does not want to have to give the cat away but really needs some help breaking the cat of these bad behaviors he has gotten into.

ANSWER: Hi, Mark. Unfortunately every action has a reaction. Meaning all the things an owner does has a lasting effect and difficult and annoying effect to deal with later. Such as giving him food when being pestered and changing old routines. He's basically spoiled and the best and hardest way to change this is to ignore him. Completely easier said than done and one way to help curb the meowing at night is to give him something else to occupy his time such as scratch posts or cat trees which she can put a little of catnip on to allure him to it. Just wondering, is there a reason why she doesn't let Dakota in her bedroom at night? If she can handle the smell, she can use a vinegar/water solution and spray by her door. The smell will deter him. I hope this helps and good luck. If you have any other questions or thoughts, feel free to let me know. Thank you.

---------- FOLLOW-UP ----------

QUESTION: Thank you very much for your quick reply.

I apologize if I did not give you complete information about the situation in my first message.  What has changed since my friend moved to her new apartment is that Dakota is no longer allowed to go out by himself anymore (he only goes out on a leash now), and he is no longer allowed/taken out after dark.  Dakota IS allowed to go in the bedroom, and the door to the bedroom is left open at night.  He does get up into bed and will even sleep right against my friend's face.  There is a large scratching post in the living room, and there is a cat tree in the spare bedroom, which is also where the litter box (or boxes?) are (in the second bathroom off the spare bedroom).

The other cat, Kabuki, seems to have adapted better to being indoors more than Dakota has.  Kabuki does not cry at the door to go out, and he does not act out to get more food.  I do agree that my friend has probably made the situation worse by giving Dakota more food when he acts out.  My friend also said that she is afraid that if she confined Dakota to the bathroom all night that he would claw at the carpeting under the door.

This is a tough situation and I guess there is no easy solution to it, but I do appreciate your comments.

Answer
Hi. Thank you for filling me in. As hard as it sounds, the best thing to do is ignore the meowing. I go through this with my own cat. She'll more at night whenever there's a change in the house. I tried talking to her but the thing that worked best was just ignore it. I still agree to find something to occupy his time. I'm glad there are cat trees and I would put one right next to the door. And add some catnip, just to allure him to it. Let me know how things go. I wish I could give a time frame but it all depends on him. It won't be an overnight fix.