I am looking to communicate with experienced PMs on the south side of Chicago that have successful working relationships with real estate investors specializing in SF properties.

I need someone that is hands on and a good communicator.

You seem to have a good idea of what you want to do, but the best thing to do as a first-time landlord is realize that everything is your fault, whether it is or not, and instead of trying to offload the problem, figure out how to create better systems or communication so that when you get to another property you don't do this again.

This is my first deal, so I’m not sure how to negotiate when my real estate agent is the only one communicating with his real estate agent.

Communication with a personal assistant is much more direct and quicker than calling a property management company and talking with an employee who works for the property management company that you may not know and that may not know any details about your specific properties or tenants other than what may be written in the notes on their property management software.NOTE: This post is not meant to offend any property managers or owners of property management companies.

If they want to offer 500k, you could say " Hey do you mind offering "500K + Processing Fee " or $497k + a 3,000 processing fee at the close of escrow " With the proper communication and deal structuring at the beginning for the most part it's not hard to get a buyer to agree to this.

I need to form better communication with bigger pockets for sure!

She is the only applicant I have right now and our communication was good so I really wanted to make this work but I don't have peace.

I have ALL written communication from the tenant where they agreed to purchase and pay, along with the attempts to collect.

I do really like her and I’m able to have clear communication with her.