Automating a website?

Hi all
I was wondering if anyone had tips for automating a website that's already earning money.

Currently my site makes anywhere from $1000 to $5000 a month, depending on my various marketing (product launch, affiliate promo etc.) but everything is pretty much being done by me and it's so stressful. I was thinking of selling the site but at the same time, if I could automate it, I think I could earn quite passively.

Some thoughts I had were:

- hiring a site manager for $xxx per month to correspond with guest writers or interviewees, edit the posts, put them up, get the newsletter out, promote on the social media accounts, some PR monitoring (i.e. HARO), managing our info product affiliate program and maybe even some backlinking etc.

- adding adsense strategically to the site once the site traffic improves from SEO efforts

Any other ideas or thoughts on automating the site so it's more 'hands-off' for me other than the selling portion or even automating income generating ideas so there is less selling altogether??

Your ideas and time is much appreciated, thank you in advance