How to raise rent by $300

[Mindi B.]

Been renting my house for the past 6 years to the same tenant. Rent is $800 and unfortunately I never raised it to keep up with market value which should be about $1100. I figured he was a good tenant, didn't give me any problems and it covers my mortgage + expenses so I'm not losing anything. (I became a landlord only because I couldn't sell it and was waiting for equity to increase. Not in it for the monthly income.) I was waiting for him to move out and then raise rent with the new tenant but he seems to be staying put. (No wonder since rent is so cheap.) But now I no longer want to be a landlord, don't want the hassle of finding repairmen, etc and looking to hire a PM. However at $800 rent I would be losing money and need to raise rent up to $1100 to cover the expense of the PM, but how do I break this to my tenant? He's not going to like it since it is such a big rent increase. Lease is month-to-month so I could just kick him out and start over with a new tenant. What would you do? (I'm not a people person and like to avoid confrontation at all costs.)