What time and day would be ideal? What are the security measures I should take or are taken by the TTC to prevent such explorations? What should I do if security finds me?
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I've actually done quite a bit of research on that exact place myself, scouted it out a few times, but I haven't yet made it to the attic, anyways, from what I've learned:
Go either right after subway service ends, (Very few trains to avoid then, but you gotta avoid being seen even on the platform since employees will know that people shouldn't be there then), or just wait until there is no one else on the platform (not rush-hour), and there are no trains coming soon, and go for it.
In terms of the day, choose one where you don't think there will be many people (weekends, day after a holiday, etc...)
Security wise, watch out for cameras and motion sensors, and definitely make sure you won't encounter a train in the tunnels.
If security finds you, I think your best bet is showing them your camera, and just being honest (you're a photographer, not planning to tag the place, etc.) Although you will probably get trespassing regardless.
Remember to constantly be wary of the 3rd rail, and make absolute sure that you aren't going at the same time a train is coming.