When I see a smiley emoticon, I tend to think that more often than not it alludes to the preceding statement/question meaning more than it seems to say.
"You look happy [smiley face]" possibly means "Whoa who ate all the pies?"
"My bad [smiley face]" maybe means "I'm pretty much the biggest ass on the planet right now."
So when the landlord texts:
"I've never seen so many leaves down the side path before [smiley face]"
it must not mean something good.
How about you give us notice before you come onto the property like you're supposed to? And how about you fix the leaking roof and let the leaves decay and return the nutrients to the soil like how nature intended? [smiley face]