Very hard on the cat IF you first let him wander outside AND then isolate him. Especially a male cat that has the instinct to roam at night.
We had at different times in our life growing up at least six females cats and then one male cat.
The male cat was the only one that went out at night roaming around.
The females were content to stay indoors.
If one intends to keep an indoor cat..then keep it indoors..In one case I had two kittens that kept each other company and avoided all that behavior that you mentioned.
Perhaps look for a mate..It has to be compatible at they are territorial.

My cats are allowed out morning only for a couple hours. I would not let Hank out if you are near a busy road. I would leash him and get him acclimated to the new area and maybe adjust his outdoor time to just an hour or couple hours, supervised. Cats should never be left outside to roam all night and I too live in Coyote and Cougar land here.

I would be most concerned about the busy road and probably would not take a chance with that. he will adjust, takes about 4–8 weeks but cats are very adaptable. Play with him more, get a laser pointer, get a big cat tree, give him cardboard boxes to play in. Buy catnip. haha
It’ll all work out I am sure.

You don’t state whether he’s been neutered. If not, that should be done ASAP.

I think getting him used to a leash as @Coloma suggested is an excellent idea which you should do starting now.

I think the danger of being run over is a distinct probability and a very valid fear on your part. My sister had a cat who had been indoor/outdoor for over 15 years even tho they lived right on a not that busy street. But that’s what ended up killing her.

Cars are totally unpredictable for cats to deal with. All the cats I’ve had over the years have been totally indoor only and lived long happy lives.

Cars are not the only things which can be life threatening for pet cats. Both Feline AIDS virus and FILV are passed primarily through cats fighting. Have you had Hank blood tested for those? What about vaccinating for those in addition to rabies?

I think the best course of action for you would be to convert Hank to primarily an indoor cat (with outdoor time only on a leash) starting now. This way he can start getting the yowling out of his system and hopefully reduces the time your new roommates are exposed to it.

Another thing which might help the situation would be to get one or more of these cat perches which can easily be attached to a window bottom and give him a view from which he can watch all the birds, squirrels and other wildlife. My cats always loved their live kitty TV.

And, of course, increase your amount of playtime with him. Ideally one or more sessions of play till he’s exhausted. He’s a young cat and needs to burn off all that excess energy.

Also, I strongly suggest doing some research on the life expectancy of indoor cats vs. outdoor. I think you’ll be greatly surprised by the contrast.

For more info. on play suggestions as well as great advice and facts about cats, go to

Jacksongalaxy.com

He knows more about cats than any other person I’ve ever encountered.

I just realized that the clips to watch are on Animal Planets website. Here’s a link.
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http://www.animalplanet.com/tv-shows/my-cat-from-hell/

Here’s the window perches I mentioned.
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http://m.petsmart.com/h5/hub?id=cat%2Fwindow-perches%2Fcat-36-catid-200061
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“Is he neutered” was going to be my question, too.

I wouldn’t take a chance letting him out near the busy road. Sad for him that he won’t be
able to go out at all but better safe than sorry. Another option in lieu of the window perch is just putting up an inexpensive shelf right under the window sill. I used to have them in an apartment I lived in. I had someone put up shelves the width of the window, and I staple gunned quilt batting and then fabric over it, so it was comfortable for the cats and it looked kind of like upholstery.

In the long run it’s better if your cat doesn’t go out. My cats go out but I always have them in the house at night or when I’m not home, and usually they’re not out for long periods of time, maybe an hour tops each day. I have a decent size piece of property and it’s not too close to the busy road so it’s doable, but I did have a male cat that, when I first moved here, I let stay out all night and he crossed the busy road to the farm across the way, and he got hit by a car.

My cat has been 100% indoors for the past 10 years. I cold-turkey stopped letting him go after he got into a tangle with another animal. He cried for weeks and tried to get out every time I opened the door, but eventually adjusted to his new, smaller (and safer) world. The only advice I can offer, based on my own experience, is to disallow him as much as possible from looking out windows for a while and to have patience. Also give him some kitty toys to keep him busy.

Oh yeah that reminds me. When I was a teen, we had to put down one of our cats who was in a fight with a raccoon. The raccoon punctured the cat’s lung and since the cat was 14 years old, the vet said the surgery would be a tough recovery. That and the fact that at the time (early 1980’s) the surgery was going to be 400 dollars, we had to put the cat to sleep.

I’m going to be completely unhelpful here. Feel free to stop reading at this point.

First, as someone with 30 years experience in emergency veterinary medicine, I’ll tell you that there are very, very few circumstances in which I would let my cat outside (I had one urine spraying/inappropriate pee-er that I let outside). Granted, my perception is skewed because we see only the worst in emergency, but I have seen soul-bruising things happen to outside cats, absolutely horrifying injuries and deaths. One that still makes me cry is the big, beautiful Siamese that was hit by a cat and dragged himself home over 3 days on his two broken back legs. The breaks were compound fractures and had dirt and grass ground in – he purred in my arms as we put him to sleep. (And people wonder why veterinarians are one of the top 3 professions for suicide.)

My second reason for not being in favor of outside cats is pretty controversial in pet owners, and that is their effect on wildlife. Feral cat populations have the most impact (1.3–4.0 billion birds and 6.3–22.3 billion mammals annually), but pet cats also take a heavy toll.

In my experience cats who are allowed outdoors tend to not live very long. Whether from being hit by cars, getting attacked/in fights with other animals, getting into toxic substances that careless people don’t handle, store or dispose of properly, exposure to disease or other various injuries. Growing up we had so many cats that I do not now even remember all of them. My parents persisted in allowing every one to be outdoor/indoor-outdoor. None of them lived long. As a kid I could, of course do nothing. As an adult I know better, and since I’ve lived own my own I will not allow my cats outdoors at all. And it’s only as an adult that I’ve had cats live longer than 2 or 3 years.

I also will not allow my cats outdoors, not only for their own safety, but also because of their effect on local wildlife (as @syz noted above).

If you choose to let a cat out for quality of life near a main road (which as a cat empathizer, I think is a valid choice), or anywhere, then you have to accept that you are letting the cat be responsible for it’s own safety in almost every outdoors situation. Mostly they will be ok, but occasionally they will get killed or lost. For some cats this will be more or less likely than others, and new situations, particularly indoor cats suddenly let outdoors, are less predictable and more likely to get killed or lost. However many/most cats do quite well at managing their own safety. No guarantees, and like everyone (even humans), everyone dies eventually, so it’s a subjective choice what level of safety vs. freedom/exploration we allow our cats (and ourselves).

I believe cats should be able to enjoy being cats under safe, outdoor circumstances.
Neighborhoods, traffic, feral cats etc. are reason for concern, but I have lived on 5–15 acre rural properties for years and have only lost 2 cats, mysteriously, ( probably Coyotes ) in over 25 years out of a group of about 12 total. Other than these two incidents all of my cats have enjoyed their rural lifestyles and lived to ripe old ages, 15, 16, 17, 18, 19.
My 2 now, ages 7 & 10 are allowed out from 8:30 a.m. until about 10:30 am when they are ready to come back in and nap for the rest of the day. I sit with them outside, walk with them down to the pond, and they are under supervision during their outdoor time.

This property is well fenced and X fenced, and their realm is the big lawn area, the little path to the bigger lawns and pond, and their favorite thing, rolling around in the expansive horse paddocks with decomposed granite and sand ground. I feel if you have a relatively safe environment cats need to experience all of their catness and we would all live longer if we never went outdoors. They like to catch lizards, gophers, and mice and voles but honestly, I think they both have caught maybe 2 birds in all their years. I love wild life too but allowing them to catch a lizard or rodent doesn’t bother me and having horses and hay/feed barns draws a lot of rodents. Barn cats are a great asset out here and many shelter cats that are semi-feral are offered as barn cats and it is a win/win IMO.

I think the real issue with wildlife is feral cats and I strongly disagree with TNR policy. Keeping dozens of feral cats in a colony is not good for the cats or the local wildlife and especially in city environments the cats are at high risk in the elements, roving dogs, cruel humans that might abuse or poison them.
If you can provide a relatively safe environment I believe that quality of life trumps quantity and I know I’d rather die doing something I love outdoors than in my recliner staring at the TV.