My DD is 3.3 and I don't let her use crying as a strategic tool. I also do not tolerate crying unless she is actually distressed. She says crying makes her feel better but having to listen to her scream sure doesn't make me feel better. BUT, I would never tell a crying child who is genuinely upset to stop acting like a baby.
Preschool hasn't been all that great for DD. She tries to engage other children in conversation but you know, that doesn't quite work well. She is quite sensitive to violence and strongly disapproves of other children's lack of social grace. She does appreciate acts of kindness but the ratio of rude behaviors/politeness is 10/1 on a good day. She is a bit disillusioned by the whole school experience but she still manages to have fun.
The best socialization she gets is through her extracurricular activities. She ends up being grouped with 4-6 year olds and she absolutely loves it.
I go back and forth between a Montessori preschool and play-based preschool. If we pay tons of money ($20,000) and send her to an exclusive play-based preschool, she'd be with children who have been carefully screened so she might find it easier to find peers. SO is very suspicious of Montessori and does not believe in exclusivity. He wants her to learn to get along with everyone but I don't know if it's fair to expect her to learn to get along with children who hit, kick, punch, push, grab, cut in line, and poke.
I wish I had a perfect solution for everyone. Sigh.