The best option for all parties if to mutually agree to end lease, and let her move out with 30 days notice.

Immediate notice of non compliance with lease.

Would the NVP be positive at $1,964.16?

Again, we don't want to be slum lords, we want our tenants to feel at home and happy.Very early on, we noticed she was testing the waters to see what she could get away with and also, I don't think she likes us holding her accountable to the rules and being around her age or younger.

Tenants moved out, very passive aggressive the entire last month after we gave notice, and they cleaned the carpets the day of move out.

Hi BP Chicago,I'm looking to invest in South Chicago and seek to establish local connections with RE Brokers and Management companies with the following experience:-must have multiple year track record partnering with investors and must own or manage investment properties-specializes in residential multi-family properties (2-4 flats)-Focus on South Chicago (East of I-90/94)If you've had positive experiences partnering with certain individuals/companies or if this is you, I'd love to chat. 

For me, I'm looking in the 90-120k range and my absolute minimum is $200/month positive cashflow (this includes management, although I plan to self-manage my first few properties).

Tenants moved out, very passive aggressive the entire last month after we gave notice, and they cleaned the carpets the day of move out.

I'm now in a position where I would like to tap into that knowledge and start investing. 

You need to look at the lease and see how much notice they are required to give not to renew is it 3 months,6 months,12 months?