Dealing with neighbor hassling me

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He is already wormed his way into my neighbor's condo and she lives alone too. However, get this, he goes over there and spends the night even though his condo is just a few feet away. Both of them have told me that they are not dating but are just friends. However, they spend a lot of excess time together. She has already has a boyfriend and I have seen him but they seem very disconnected but she seems close with this neighbor.

Wow. People can just make amazingly poor decisions. It is amazingly immature of your neighbor to spend time with this guy given what she knows or should know.

The guy is a hothead. And from separate reports, almost certainly abusive at times. But, he might be charming in other regards. Now, as far as helping your neighbor, there may not be a whole lot you can do. Often understating the case works best. Especially if she brings it up and you might say something in understated fashion like, ‘I’ve heard stories that he doesn’t always treat people right’ or similar, and pretty much just leave it at that. Getting in any kind of argument with her is probably a losing proposition.

Now, if he is engaging in stalking behavior toward you (and it’s always kind-of, sort-of stalking, hardly ever ‘textbook’ stalking) then any kind of interaction with you, whether positive or negative, counts as positive reinforcement toward him and his behavior.

It sounds like the Condo Association knows much of what has been going on, but has not really made an adequate response to the whole situation. It’s a shame they can’t send another guy, about the same size as this guy in order to reduce embarrassment, to act as your intermediary, and just matter-of-factly tell this guy that you simply wish to be left alone.

He is actually a rather small and skinny guy and so it wouldn't take much for a bigger guy with guts to intimidate him, lol.

How does anyone feel about me speaking with a neighbor or so about this guy?

Talking with the neighbors is okay, as long as it's done with a light touch.

And, with the guy not being all that big, I do recommend ju jitsu. Maybe one private lesson the end of this week and two lessons next week, and you might really be able to learn foot-stomp and grip-breaks. Practice does help. And it might make a big difference if needed (still want to practice good avoidance behavior of course, never underestimate any opponent). And it does give one a certain confidence level.