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At first this may not sound related but hopefully you'll see towards the end it does in fact tie in. :)
Car dealer had a Ranger I was interested in. They originally wanted around $5,000 for it and this is supposedly a no hassle dealer, their final price is marked on the windshield etc. After driving it, I immediately determined it needed a clutch.
I told the salesman I'd give them $4,200 cash. Of course he had to take the offer to the manager and all that happy dance so I gave him my phone number and left, telling him not to call unless they'd accept $4,200...don't bother calling even if the counter offer was $4,201.
Next day I get a call to come back to the dealer and sit and speak with the sales manager. I agree as it's near home and on the way home from work. Manager tells me the price is still the original $5,000 and I'm instantly hot that they've wasted my time. Salesman was standing right there and I told the manager I specifically told the salesman not to call if the price was 10 cents over my final offer.
Here's where it reminded me of your landlord story. The manager said he "played the odds" that they could convince me to pony up on my offer and also the odds that I hadn't so thoroughly researched the value of the vehicle! I told him what I thought of his practices and left with no truck. They dropped the price to $4,500 a couple weeks later, no idea what it finally sold for.
Sounds like your landlord "plays the odds" that most tenants would accept his terms without questioning the fairness. Each time he gets away with it he's ahead and when he doesn't he still breaks even, pretty good odds.
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