We've owned the cabin for almost 9 years and have utilized a management company to run the every day business.

A primary residence is where your mail is delivered, where you have utility bills in your name mailed to that address, where your driver's license says you live, where your w-2 and IRS etc. are filed.A second home is a part time owner occupant and is usually 100 miles away and in a resort area.Four units in another state while you own single family where wife lives is not owner occupied. 

Apps such as AirDNA, Your Porter, Google Suite, Zapier, when utilized together can effectively handle the 75% leaving you to simply take up 25%. 

Tax returns, banking records to show income coming in and bills, rent, utilities going out.

Buy or inherit and hold all their lives while working the properties for income.I've seen teachers, firemen, software engineers and all sorts of people utilize both strategies successfully.

If she still needs help there are programs that help the renter pay for utilities and rent. you can offer that as an option.

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.