Tenant Newsletter: Does anyone do this?

[Will Gaston]

All:

I've got about ~150 college students that are currently renting from me and am considering sending out (via email) a regular newsletter.  Purpose being to enhance communication with my communication adverse tenants which happens to be every single one of them. 

A few questions:

-Can anyone recommend a website or service where I can automate some/all of this? Possibly one specific to property management?

-What types of things do landlord send out with their newsletters? 

-Is monthly too often to send it out? Am hoping they will actually read it so don't want it to seem like spam.