Outdoor-cat-to-indoor-cat transition

I am sympathetic. I have two that lived from birth to 8 or so weeks outside. I brought them home and they haven't been outside since. When discussing the indoor/outdoor thing, a friend told me essentially that indoors only is inconsiderate and asked me how I would like living on one room my whole life. It stuck with me and I felt horribly guilty for awhile. But, bottom line, there's a trade off: adventurous, possibly short life or safe secure long life. Bottom line? This ain't the wild west and open prairies...it's a damn dangerous, toxic world out there. And life out there is hard on the wee ones. When confronted by outdoors-rightsists, I simply say I haven't the constitution to allow kitties to roam free. I would freak at every car squeal and every yeowl. We built a screen enclosure outside of our front door, as a kitty escape buffer zone. Floor to ceiling screen...they love it. Bring in rocks and leaves for Magnet to roll around in. Pick up some leaves or whatnot from the ground where you work or from other places so Magnet can smell new smells. Nthing Feliway...never had to try it but I've heard it works wonders. And do sit down with Magnet as jbenben suggested and explain to her why you are making the change. It makes a difference. There are also cat enclosure-type products...kittywalks, that may be useful. You may want to wait on those, though.

UPDATE!! He's been inside pretty happily for a couple months. It tends to agitate him a little bit more to sit in doorways and windows when they're open (he watches all the big fat squirrels run around in the yard, and wants to chomp them), so we have a lot of places for him to hang out that aren't right near windows, in addition to lots of places where he can sit in the window. The nighttime meowing has gone down a lot, and only usually happens if he needs a refill on crunchies or wants to announce to me that he has captured a toy. What I have found that seems to be the magic combination is: we play a lot during the day with lots of running and jumping, I snuggle with him right before I go to bed, make sure his box is clean and the dish has some food in it, and then he sleeps through the night (or at least entertains himself) 8-9 nights out of 10. I haven't used a leash or harness or supervised outdoor time yet, but am still considering it at some point. He's only "escaped" twice or so, and he just runs out on the porch and rolls around (as opposed to taking off down the block), so I trust that he's doing fine. He no longer tries to run out the door as people come in or out, and he's very content to hang around in his favorite spots in the house (the doorway of my bedroom! he's like my own personal bouncer). I also still don't use a spray bottle. His mental health is perfectly fine, and he lets me know very often that he still loves me a lot.

for health and safety reasons What about his mental health? We'd all be safer if we never went outside.

"If I sprayed every human in the face who annoyed me, I'd do nothing but that all day." Best. Idea. Ever.

I don't have any interest in punishment-based attempts at conditioning You sound like a great cat-parent! I can't tell you how much I dislike the idea of using spray bottles on cats. I think you'll be going through a lot of trial-and-error based on the responses here - let us know what works? Good luck.

I'm not even interested in starting to use a spray bottle because 1) I don't have any interest in punishment-based attempts at conditioning, and 2) my cat doesn't really do anything "bad", just annoying. If I sprayed every human in the face who annoyed me, I'd do nothing but that all day. I can deal with being annoyed.

My understanding about the squirt bottle is that in these cases, it acts as a negative reinforcer of the behavior. I've also read and heard - and my own experience has borne this out - that it's ineffective for behavior modification beyond getting the cat to stop doing what he's doing while you're standing there threatening him with the bottle. We initially tried the water bottle for our night meower. It worked for several minutes. Your cat may vary.

A note about squirting your cat with an air can or water bottle: I've seen comments here, and elsewhere on metafilter, about what a terrible idea this is because it just teaches your cats to fear you. I was reluctant to use this method, and so put up with being walked all over every night until my husband moved in. He was insistent that we use water bottles, and you know what? My cat, at least, seems smart enough to know the difference between human+middle of the night+water bottle in hand and just a human alone. Heck, he's fine with coming up into the bed when he's invited. This extremely brief reprimand hasn't made Sam Katz fearful of us at all; he just seems to really, really hate being squirted, and it helped us move away from a routine where I was waking up every night at 4 a.m. to let him out. That being said, we don't have a door to shut our kitty out; since you do, earplugs and ignoring him is probably the way to go. Oh, for leash walking your cat: mine just squirms his way out of normal harnesses. A http://www.catwalkingjacket.com/ tends to work better for slippery kitties.

You've asked about night meowing. I'm going to copy and paste part of an http://ask.metafilter.com/142297/Girlfriend-Cats-and-I#2038857 I gave to somebody else a little while ago. "That's another difficult one to eradicate once you've allowed/reinforced it. We have a night meower that we have [...] cured of the problem. If the ear plugs and white noise won't be sufficient, you'll need to take some steps to stop the behavior. First and foremost: do not reinforce their meowing by personally responding in any way, positive or negative. Don't talk to/yell at them, make noises at them, squirt them, or open doors for them. That's going to be the hardest part. If you have a way to make a loud, unpleasant noise that cannot in any way be associated with you, go ahead and use that when they meow. Keep them alert and active during the day, especially in the afternoon/evening. Get cat toys they love, leave them around the house, and trade them out on occasion. Hide treats around the house for them to find. Wear the cats out by playing them at night before you go to bed (think laser toy or "da bird"). Leave toys in the area they meow at night. Along the same lines, give them attention/affection during the day and especially before you go to bed. [...] Brushing them, petting them, talking to them, and allowing them to sit on your lap all count. Make sure they have a comfort zone at night, such as a soft bed in an area away from any noises or disturbances, such as a central air vent. Close your blinds and curtains to block any outside stimulation. You may want to consider using http://www.feliway.com in their comfort area and in the area they meow at night. So, night-meowing summary: activity and attention during the day, quiet area and an outlet at night. Ignore the meowing when it happens."