The other half of the accounting records is coming from online purchases, utility payments, etc etc where they are sending you an email. 

We want to travel and invest and are considering converting this short term rental to a long term rental to avoid sales tax, paying utilities and general management of the property. 

You'll find a ton of kind, supportive, and helpful people here.Are your existing 7 properties currently in Chicago? 

Most investor utilize short term hard money debt to scale their flipping operations where the lender will fund 80+% of the purchase price and the rehab budget which can allow investors to work on multiple projects at once.

I'm used to paying a 10% management fee in other markets that covers the costs of paying utilities, etc., but RHR charges $10 per bill payment, a fee for renewing rental registration, fuel surcharges for service calls, etc.

Real estate investing meet ups (Bigger Poclets events and Meetup.com)- Both BP and meetup.com have a ton of opportunities for real estate investing and just networking in general.

There is a ton of liability still with that option. 

I hired a GC to manage the build out, but there has been no consensus on who is responsible for the utility payments (Water and Energy). 

Also, I always keep a few generators handy—trust me, it’s saved me (and my tenants) a ton of headaches!

At one time they were trying to figure out how  to finance a $10,000,000 roofing and siding project but got bogged down with attorneys and all the mess that goes along with a project that size.