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She also lets her dog wander around by itself, and she walks around in cold weather gear while it's like 70 degrees, which freaks out my wife.
Stray, unleashed dog -- you can probably do something about it. However, you're obviously dealing with a mentally ill person whose only friend on this world is probably that dog. Pick your battles. Explaining the law or HOA rules to someone who is mentally retarded simply does not work.
There are bigger battles to fight when it comes to severely mentally ill neighbors. That's the "do the friendly neighborly wave" until the neighbors either can't financially support themselves in your neighborhood or finally realize that they can't take care of your mentally ill neighbor and have to put the person in mental care.
Your neighbor is a bully. You won't have a good relationship with him, period. The sooner you accept that the better- what you need to do is manage it. Ask about him, but don't make it obvious, be very discreet. Some of the other neighbors are probably afraid of him and don't want to end up on his bad side, and others might actually rat you out. Best thing to do is avoid transparency. Eventually you may have to stand up to him, but make sure when you do you have some actual leverage and be ready for him to react badly.
Remember that you're not dealing with a fair and reasonable person - you've already established that. Don't try to play nice with him and expect him to go along. He'll just take that as a sign of weakness.
If you want to deal with this issue in baby steps, I support the people who have suggested telling the HOA. Specifically mention that you are aware of the rules against leaving bins beyond the property line, and you are writing them because you don't want the neighborhood to think poorly of you or for the HOA board to see you as some sort of scofflaw. If you want to maintain maximum niceness, omit your knowledge to whom the bin actually belongs. I would do this in writing and with an enclosed photo.
If you want to up the ante, cc the next door neighbor on the letter, but still leave out who the trash can owner is.
If you want to take it up a notch, include in the letter your knowledge that the bin belongs to your neighbor.
All of these avoid a direct confrontation, and allows you start from a very low level of action. It will also protect you from receiving a citation from the HOA board at any point in the future.
Wow, sounds like CREEPY-DUDE-Neighbor is NOT putting his can on your property,
CREEPY-DUDE-neighbor is actually not doing anything wrong.
Sounds like the OP is over-reacting, wow, I thought I got wrapped in knots over little things!
I have come across a LOT of Women who are afraid of their own shadow.......so in their world they see any guy who is not spit & polish as a creep, weirdo, child-molester, threat, etc, etc, etc. I am NOT saying the OP falls into this category...........but, the theme of the story sounds familiar.
I really like the idea of taking the can. . ...I just wonder if he's crazy or something. I don't want to stir up even more crazy. I don't want him tossing things over the fence or other actions that he might consider retribution. I think I'll end up knocking on his door to ask him to stop.
Do you have a truck or access to a truck. Wait until it's dark and just let the neighbor's trash bin disappear, a stealth operation. If another trash bin appears, abracadabra it disappears. If asked, I don't know nothing!!
Ask him to move his trash can and if he invades your space again, tell him to gtfo.
If he makes snarky remarks, warn him once that the next time will result in loose teeth and to not bother you any more, ever again.
I seriously value the time I spend in New York City as the most valuable learning experience of my life. Prior to that, I too was a sniveling, wrist-flapping, passive aggressive woman worried about other peoples 'feelings' or what they might think of me. Live in a place where those people get eaten alive, you earn your whiskers real fast.
Having a good relationship with neighbors is always nice- and to be sure, I give neighbors a MUCH wider berth than I do any other random person simply because they're neighbors- but the slightest hint of of hostility or disrespect from them, I have no problem making it so they quickly realize they've made a terrible mistake and to go bother someone more like the majority of impotent whiners in this thread.
Just ignore it. If there's no reaction where's the fun in it for him?
Or he's mentally ill and there's no real solution.
Or you could follow Zaba's advice and threaten a knuckle sandwich. Sorry, I'm laughing!
If you ignore this guy it can escalate regardless of what you do, unless you do what you should, deal with the trespassing issue.
This is not the time to be touchy feely. Writing letters and getting neighbors involved or doing so anonymously, as if he isn't going to figure it out is risky.
Face it, the guy could care less. If you file a complaint with the police, if something does happen, you are first in line, not the victim wondering what happened and why.
Look at it this way, he is Putin. Act like Obama and see what happens. It is predictable.
In most HOA the trashcans have to be removed from site within a sit amount of time.
Personally I would do nothing since I doubt I would even notice such a thing unless the can was on my properly or I could smell it from it.
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. ...I just wonder if he's crazy or something. I don't want to stir up even more crazy. I don't want him tossing things over the fence or other actions that he might consider retribution. I think I'll end up knocking on his door to ask him to stop.
If another trash bin appears, abracadabra it disappears. If asked, I don't know nothing!! 
