Do I need to file a 1099-MISC?

[Brian Pleshek]

Greetings everyone.  

I've had a SFH rental for over 15 years and have always done the work myself or paid a company like RotoRooter to do the work. This past year, I acquired another property and put in 15k-20k in updates, but this time, I used a contractor. This is a "guy" I found in home depot and he agreed to do the work. He works for others, so I don't think I need to deal with the issue of whether he's w2 or 1099. But my question is, do I need to file a 1099-MISC? My wife doesn't think so but I'm thinking we do since we gave him more than $600 last year.

Assuming that I do have to file it, how do I do it?  I can go down to staples and get a form and put it in the mail to him.  But do I need to send it certified or return receipt to prove that I sent it?

As far as filing with the IRS, do I do that electronically or do I just mail in a copy to them as well?

Thanks,

Brian