travel with semi-feral or give him to a colony?

I would love some advice on whether to give away a young neutered male to a colony or keep trying to socialize him (if so, for how long). Sorry for the length of the post -- it seems important to explain the situation fully.
   
We live in a small apartment in Mexico with our dog, three permanent cats and ... Rasputin, a 8-month-old kitten we pulled off the street and neutered. Although he has improved a lot since we got him, he still hides most of the time, avoids being picked up and runs from us. He is in love with one of our cats and follows him everywhere, imitating him, but is indifferent to the other two. He is curious about us and will approach us, and, if cornered, can be picked up and handled (though he usually stays tense).
   
In about 7 months, we are heading back to Canada, where we will have to live in an even smaller place -- and because of the temperatures outdoors, our Mexican street mutt will also come in to live with us.
   
The rescue group we volunteer with here in Mexico has a small ranch with 30 cats, who are fed and cared for as well as is possible with outdoor cats but I am still a bit leery, especially because of the many cases of cat poisonings in the area.
   
1. How stressful would a transition to Canada be for this kritter?
   
2. Would he be happier in our little Noah's Ark, or taking his chances at a fun outdoor ranch with 30 cats (who are getting fed, and do receive vet care), but no human contact to speak of?
   
3. What are the chances he'd panic and run away from a cat colony?
   
4. He's VERY attached to my neutered male...will he be able to make friends at a colony?

You ask, I answer...
   
I'd take Rasputin with me. Given a choice bet.my (slightly crowded) home & a cat colony in Mexico, I'd take him out of Mexico. Let's face it, Mexico isn't very stable or safe these days, & when there's social problems like theirs, cat colony care is likely to end up on the bottom of the list of things to do well. And there's no way of knowing if he'll run away from the colony.
   
Are you flying to Canada? If so, see if you can keep the cats in the body of the plane as carry-on luggage - & the dog, if it's small enough.
   
My choice of transport: Drive to Canada; you may want to consider this. It would be about 4 days, I think (abt 2000 mi.), but you can rent a lg vehicle, like a van (if you don't own a car of your own), pack as much of your stuff as you can into it, & load in the pets. Or you can rent an RV & tow your car beh. you, thus eliminating the need to find hotel rooms every night.
   
You can have a moving company ship the rest, if there's enough. (I recommend contacting Interstate Van Lines, ask abt their moving options bet. Mexico & Canada. The company is family-owned and are very careful who they contract with for their moving contracts outside of their immediate area - they have a website. Or use some other huge national brand that has a track record.)
   
The PetsWelcome website (link below) lists pet-friendly hotels, motels, cabins, resorts, campgrnds, cottages, & B&Bs, fr. lg chains to little Mom&Pop motels to KOA campsites.
   
Rasputin's transitioning fr. feral to domesticated. He's thawing out & getting a bit more social, so there's hope for him. Just don't push him - cornering him doesn't help, it just makes him more reluctant to have contact. Let him come to you. It can take a long time for a feral cat to settle down in a normal home. When he wants affection, when he realizes that His Idol is getting attention & he isn't, he may just come over & ask for some petting.
   
Since he loves your neutered male, he has a good role model; I wouldn't want to separate them. I think he's better off with you than in a mob of strange cats that're probably wilder than him by now (after all, you can actually touch him now). There's no way of knowing how well he'd make new friends. As for the other 2 cats, indifferent isn't bad - at least he's not starting fights. He may never be friends w/them - or he will later when he's more confident of his position, after all, he's only a kitten & new to the clowder.
   
If you're not keeping him inside all the time now, start this right away. Get him (& the rest) used to not going out - cats live 3-5 years longer as indoor cats, & he could easily get lost when you get back to Canada if you allow him to go out.
   
Get all the pets used to living together in the small space of the apartment, so they aren't shocked when you move back to Canada. There are window porches you can install in your Canada apt where the cats can watch birds, & if you have any patio or balcony, you can buy or build a cat exercise pen for the cats to play in when the weather's nice. (Instructions for cat exercise pens can be found by Googling "cat pen plans OR directions" or some similar search.)
   
Helpful, I hope?
   
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You're a marvel - and thanks for the detail!
   
All my cats are already fully-indoor (they're also being human-toilet trained), and you'll be thrilled to know Raz is doing well with that, too. Dog's the only one who lives on the patio.
   
I will definitely check on the land travel, though we have so little stuff and are not very well off (bf's a med student) that it might be a bad idea financially, especially with so many animals on the road and with the US border to cross (ew) and Mexican police to bribe. I have looked at flights through Mexicana, and the trip to Vancouver can be made in about 14 miserable hours, with a non-stop flight from Mexico City (6.5 total hours in the air). I think land travel to Whitehorse, Yukon might be more like a week... of sheer unadulterated hell.
   
If we end up having to do the air thing, do you know whether cats cope better traveling in pairs in a carrier? Mexicana can be talked into this option, and it might make Raz a bit happier if he can travel with his Big Brother. Should I just buy crates now and start working at it?
   
Seriously, any further advice is greatly appreciated...you already did a great deal to help me make up my mind!