Does he have to report the income he received this past year and declare it a rental event though he would like to move back in eventually?

We plan to convert the sale proceeds into multiple properties to create passive income. 

It appears they calculate gross ROI based on gross income divided by property price.

High crime + low income = Poor tenants to choose from.  

I've posted extensively about coastal Oregon vacation rentals and their challenges and production potential, typically a strong STR will generate roughly 10% of valuation in gross annual income. 

Don't forget about loss of income/rent...that being said this is a very broad question and I'm not certain if you think you have too much coverage or it costs too much or both...

Reed and tell him Jason Wray sent you he is over by my Corporate office. 

We aren't necessarily concerned about a monthly profit on our first 10 or so as we are thinking these would be held for at least 10 years.So, a question we have about 2 houses - House # 1-smaller,good area new roof, new window, no basement, no garage, monthly income $140, $6000 left in debt to heloc..........House #2 - larger 4 bed, 2 bath, forclosure, estimated rehab 40k, estimated monthly income zero, zero debt to heloc........ higher value home.  

I am glad you mentioned to lending aspect of not having the W2 income.

It connects my airbnb and VRBO calendars, offers automated messaging, smart lock integration, cleaning calendar/reminders, and offers pretty good income reports.