re: Complicated situation. Advice appreciated. Will try to be brief.

I agree with the poster that said it sounds like you have feelings for her but you know it is a bad idea. You stated a couple of times that you are concerned there is a "father figure" thing going on. Of course there is, and even though you may regret it now, you have probably promoted the father figure role. There is no other reason that you should know that much information about her personal life unless you have somewhat enjoyed participating in the father figure role and trying to give her advice. When women at work start talking personal business, get the hell out of the room!

Now, as things are coming to a head, you see that it was poor judgment to get this involved in her personal life but you can't just undue what you have already done. Perhaps the soon to be released boyfriend is what has brought the matter to its current unmanageable situation.

You need to have a conversation with her, with a witness present, and let her know she can't just hang out on your property. If she does not take the kind warning, then try the sheriff's department. However, that only works out if you have honestly not led her on in any way. Otherwise, you've got problems.