He is month to month, and I let him know I am not going to have him here for September (i.e. 30 days notice, so August would be his last month).I would like to get him to leave sooner if legally possible, for my peace of mind and the safety and comfort of future tenants, if I rent other rooms in the house.  

If they are less-than-ideal in any way, then I'll be a little harder on them like only paying for portion or paying for the entire thing but then giving them notice of termination.

@Cody PetersenWe could likely make any of those evenings work with enough notice!

I would send a notice out and kindly reiterate the parking rules and the penalty if not abided by.

I also noticed with our housing market data that people from Boston are moving to Portland ME.

To my knowledge, this is the extent of what the city requires regarding notices. 

-Completely notice to quit/evict?

She recently lost a newborn baby and everything has been downhill since She has stopped communicating with me for over three weeks now, has missed her last rent payment, has let the house go completely to hell, and I just got a letter from the magistrate that I have a court hearing over the amount of trash in the backyard.I posted a 30 day notice on her door being that she is month to month.

From NOLO:Amount of Notice Connecticut Landlords Must Give Tenants to Increase RentConnecticut landlords are not required to give a particular amount of notice of a proposed rent increase unless prior notice was previously agreed upon.

He usually breaks 2 things while repairing 1, makes decision without telling anyone and takes random days off with no notice.