Yeah - it’s not actually.

What’s so difficult to understand? I want to go on vacation - I want to sublet my apt for 3 months - he says he won’t let me (he has the right to refuse and I can go to court if I want in his words) - he tells me I can leave if I don’t want to pay the rent and if he finds someone from November (likely as he has 2 ppl asking for an apt), he would return my last month rent which he says he doesn’t really have to - if he doesn’t find someone for November, I’m liable for that months rent, same for December, Jan, Feb and March - my friend finally speaks to him and asks if a guest can overlook my apt while not here - and he’s forced to say YES and asks me for 3 months of post dated cheques and have someone else staying instead of me during that period, provided they cause no issues, maintain a low profile and don’t use any common areas of the building.

That's quite a sentence.

How about you do whatever you feel is best and then sue your landlord if he doesn't give you your money back?

^ I already mentioned that he’s okay with the “house-sitter” guest arrangement. I’ll only be gone for 3 months.

lol @ OOT. Good mix of derisive tone and being 100% incorrect. Nothing is intuitive about Ontario's tenancy laws.

The real answer lies in your condo rules. Some condos allow it, some don't. For a couple hundred dollars I could get you a real lawyer to review your stuff.

If you don't care about giving up post dated cheques (which he can just cash immediately... *cough*....) then whatever I guess. I'd probably check the rules w a pro and go through the sublet process.

The last 3 apartments I lived in all had something in the lease against it. I live in a Midwestern suburb, nearly every apartment I looked at disallowed it. My buddy lives in NYC and it sounds like subletting is a lot more common there, probably because rent is stupid expensive and leases that go for more than 12 months are more common.

This is interesting, though from a 6 year old article.
"If a tenant has assigned or sublet without the landlord’s permission, the landlord has 60 days from discovering the new tenant to apply to the Landlord and Tenant Board to terminate the entire tenancy. If the landlord does nothing, then after 60 days, they are deemed to have accepted the new tenant."
https://www.thestar.com/business/rea...ubletting.html

If that's still accurate, he can either deal with it or let you out of the lease. I doubt the laws are that renter-friendly in the US.