I know of what you speak.1) I'm surprised the Sheriff said you could not press charges for trespass. I thought if it was your property, you can trespass anyone you want.
2) I live Massachusetts (aka Liberal sh!thole). Sadly, I can count a few different instances there in your story where the trespasser would be pressing charges on you and the Sheriff would have you in cuffs.
Democratic People's Republic of Taxachusetts!