If you've got multiple properties, do this full time, manage your own and generally run it like a business (ie, you take deductions for meals, mileage, phone, internet, etc.... beyond just "investment" expenses), then I'd argue that you're running it as a business and should 1099.But really, when in doubt, 1099. 

I've spent hours browsing the internet and I'm getting a lot of contradictory information. 

The first step with any brilliant idea, before protecting it, is to share it on the internet.

I asked him if he could help pay for utilities, internet and Netflix. since his occupancy was sure to rise the utility bills.

@Fred CanzanoIt really is time for you to get off the internet and onto the phone with a plan professional and your tax advisor. 

They’re all over the internet to buy.

I am just some dolt spouting opinions on the internet that may or may not have any value, use for entertainment purposes only!

I can dig into these cities all day long on the internet, but because I'm going to be living there as well (not just out of state investing) I plan on visiting these cities before making a final choice. 

Find via an internet search.

Unable to Deliver Marketable Title Return of Earnest MoneyA friend of mine, Kevin, recently is in a situation which I cannot seem to understand fully, but am hoping a Real Estate Attorney can shed some light on the subject.Kevin searched the Internet and found a property that he wanted to buy.