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Schroeder knows, deep down, that this fascination he has with a crying Lucy van Pelt probably makes him a bad person.
He just doesn't care.
When Lucy cries - actual tears streaming down her blotchy cheeks which she desperately tries to blink back, to no avail - she is no longer an untouchable queen. She is mortal, just as breakable as the rest of them; she is real and much prettier than when she is all haughty and proud. He wonders if he'd ever told her that. Of how human she is when she shows emotion. It showed that she still felt, still cared, still hoped. He knows that she'd overdo it if he did, though, and so never tells her. He doesn't want this wonderful thing backfiring.
Schroeder knows, deep down, that being the reason for someone's tears is probably not a good thing.
He just doesn't care.
When Lucy cries over him - too distraught to speak, to think - it shows that she feels something for him. Something more than the horrid lust, the infatuation. Something deeper, truer, more. Beethoven had been a man of emotions; it is only right that Schroeder is too. And so he develops an appreciation for Lucy's tears, because it's a sign that she loves him. And that even though they had such a turbulent history, Lucy still hoped for something more, still hoped for him.
It was nice to be wanted.