And pay all of his own utilities.

He keeps utilities in his name so he can shut them off if the tenant isn't behaving.

Have any of you utilized Hometap?

Once you buy one, you'll probably buy more.Some suggestions:1) Us Quickbooks and set up Classes for each property and subclasses for each unit. 2) Scan EVERYTHING to either Google Drive or Dropbox. 3) Create a consistent folder-tree convention, example:   Main_123 (property address with street name first)   -General Property Info   --Insurance   --Property Taxes   --Title Docs   --LLC DOcs   --Purchase Docs   --Loan Docs-Utilities-Maintenance-Leases   --Folder (LastName_FirstInitial)-Advertising-Rental License-InspectionsAppliances & Mechanicals (pics, model tags, warranties, etc)4) Create list of consistent naming conventions for files so you don't have to open themExample: yyyy-mm-dd Main_123 Water Bill mm-dd to mm-dd $xx.xx               Lease Main_W_123_#unit (LastName_1stInitial) $RentAmount EXP yyyy-mm-dd5) Create a great lease by reviewing several from online, then have attorney review for compliance with state & local laws.

Why set the lease to start tomorrow if he wont be utilizing the room for another 3-4 weeks?

Use a copy of the Quit Deed to show the proof.Update everything associated with your business (utilities, bank accounts,...) to the LLC name 

So how do I make my tenets pay all the utilities?

One big takeaway for me personally, would be to utilize the help of a licensed professional commercial realtor to negotiate on my behalf, going forward.

I wouldn't include any utilities in rent if it can at all be avoided, even with solar. 

Owners with 40+ units tend to have more expenses (maintenance, utilities, etc.) and are more likely to have tenants that pay late, so we try to wait until the majority of funds are received before paying them.