We can help with collections and utility billing automation.

If you buy in a nice part of Chicago it's pretty easy to self manage after you move out using services such as Cozy for rent collection (it's what I use and automates the rent collection). 

Highly recommend "Airbnb Automated", "STR University", and "STR Success Stories", on YouTube. 

So set up a automation system (REIblackbook.com) to stay in contact with them with out you wasting to much time. 

@Alyssa Czopor I use the following to self manage remotely: keyless entry, wifi thermostat, ring flood camera, iPhone, Airbnb/Vrbo, Beyond Pricing (dynamic pricing), Your Porter for automated guest communication.

Other than that, we plan to add value through systems and automation (old owner used to do everything himself) What was the outcome?

I am specifically looking for a tool to automate maintaining the agreements in the lease and communications with tenants, as well as a ticketing system for maintenance requests, maybe a capitol improvement request functionality.In my wildest dreams I would find a consultant someone local to central Massachusetts who would come in and see how the portfolio is currently being managed and make recommendations on accounting and property management systems and processes for our team to evolve.

No way in hell I'd ever work with someone that left me an automated RVM 

I’m going to cross post this in a few places, and to be clear, I am NOT talking about software or a bookkeeper that specializes at any of the following:bookkeeping for taxesrent roll and property managementproperty purchase assessmentrenovation budgets and build managementtraditional stock market investmentsbusiness managementpersonal financesI am looking to take information from all of the above areas and create a holistic cash flow, net worth, short term and long-term automated projection of EVERYTHING all at once.

I’m going to cross post this in a few places and to be clear, I am NOT talking about software or a bookkeeper that specializes at any of the following:bookkeeping for taxesrent roll and property managementproperty purchase assessmentrenovation budgets and build managementtraditional stock market investmentsbusiness managementpersonal financesI am looking to take information from all of the above areas and create a holistic cash flow, net worth, short term and long-term automated projection of EVERYTHING all at once.