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Free feeding (through a feeder) is not bad, but it wont work for every cat, you can try it and simply stop if your cat does become fat.

Otherwise you should have 2-3 feedings per day for your cat, give him half his food in the morning, and then the other half of a full days food at night, and in the middle you can give him a nice little snack/treats. If it's a very young kitten under 3 months, provide 24/7 access to dry food, and give him wet food at least 3 times a day.

How much to feed, depends on your cat, and what food you are feeding, if you feed something like Friskies or Purina Cat Chow your more likely to dish out 1 - 2 cups a day. On a food like Felidae you'd only be feeding about 1/3 - 1 cup a day, once again, depending on your cat.

As for raising a cat lovingly, each cat does have a personality so you can't 100% mold it to the vision you have of the ever loving cat.
However, start by spending most of your time with him, if he wants to sleep tyr to convince him to sleep on your lap, you are the best spot, you are the safe/comfort zone. Accustom them to you touching everything, every part of their body (this will help with their tolerance of things.) Play with him, give him good treats when he sticks with you or does something good, and teach him to come to his name, so you can simply call him and have him be with you whenever you want.
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