Formerly a Queens Pirate, now a Kings Pirate. I know this sort of world well. I've learnt a lot from undercover detectives as well.
Peccary is indeed right. As a kid in the Druitt, through the tiled roof, is the easiest. But I never used the break through the plaster ceiling method. Only morons did that. I always used the foxhole to get down and my rope to get back up, replace the board back in and replaced the tiles back in. Never knew I was there, but I'm sure they wondered where their food in the fridge went.
There are two types of Thieves. 97% are the lazy, stupid easy meat thieves. They are scared of hard work and mostly incompetent if they go for harder acts. If they see something that looks like hard work, they usually are easily deterred. These are the ones that if they see a padlock on the gate, they don't bother to check if the padlock is actually locked.
Two weeks ago a local Security Guard invited me to his house with an amazing sea frontage that costs millions in Sydney, but only $900,000 for him. He asked my advice on his home Security efforts. Like about him getting a 4-digit keypad lock.
I told him to get a 6-digit, because it takes me just an hour to go through the combination to eventually hit the code from either direction. Just like those old bike chain combination locks and briefcases.
But the other Thief, who is of more professional in his.methods. Well, you can't really beat them up to a point. But only very professional entities employ these guys and there's usually a good reason why they got into your house. I've met the best in Australia and well, the trick of it is 'Time'. A good Thief makes the time. A Bad thief tries to rush out of fear and paranoia.
I remember in my teenage years, sneaking into the local quarry kitchen at the old Erskine Park site before it became an Industrial Estate. They couldn't work out who or how their chicken wings, cakes and beers were consumed on and off with a little note left by Santa saying thankyou. They couldn't see any forced break and enter and the door and window locks were updated each time, I saw. They even had a Security guard in a car at night, keep a watch.
But even as a teenie. I still could just casually get in (took 20mins in and 20mins out), munch out, get some nice cold ones down and guess I got another Security guard sacked who for the life of them couldn't see me at just 20m away.

I never did get to note them, that I removed the entire window itself, put it aside and put it back in 'securely'.

Oh the fun and games of it all. I'm sure you remember one of my favourite memories. Of me and a mate living in Kirribilli and after the 3am round of the local cop patrol. We just strolled past the sleeping Security guard and into the Lodge (Keating). But I swear on my mother's knitting, that we were not responsible for that photo of the sleeping guard on the front page of the Daily Telegraph 3 days later.