You can switch to a lawn service and the major issue will be they have to move their stuff when the lawn guy comes.  

If they see you working hard and serious about investing, maybe they will help you move forward.

Chicago real estate is moving quickly and it's honestly no surprise rents are too...with less inventory for sale that also means more people are forced to rent, which in my opinion would drive up the rent.  

I currently own a home in Hawaii, unfortunately my family and I are moving and we want to make the correct choice.

You are making the right move by going to RE, IMO.I think you have the right idea on the strategy. 

When a tenant moves out, transfer the deposit back to Checking so it's ready to apply towards expenses or refund the Tenant.If you end up with excess funds in the Checking account, I recommend you transfer it to a third account designated explicitly for future investments.

I am even willing to overpay for some great helpI think those 4 are good for now, feel free to answer 1 or none if they sound silly lol.Thanks in advance and look forward to connecting more with folks on here!

I usually don't chase bad money with good and agree that your $20k against a 6 figure monthly bleed won't move the needle.

At this point, I just have to stay the course and keep moving forward.