Thanks everyone. I actually got to have a decent conversation with Joe (my b/f) last night.

We have decided to do a few things different. Because Handsome used to be an outdoor cat (and by process of elimination he is most likely the culprit of all/most of these problems) he is now an inside/outside cat. Hopefully this will burn some of his energy & make him use his brain a little more, pretty much give him the stimulation that he needs which will hopefully make him more calm & well mannered in the house.
We will be keeping track of what happens, see if anything triggers any bad/good behavior etc...
And we have a few more products to try if need be.
And Joe will be more responsible about cariing for them and the like.
We will be setting like an evacuation or outside cat ONLY date, probably about a couple months down the road, which will give us plenty of time to try out the other products & see if something actually works. I think this is a fair opportunity.

Of course if things happen to occur when everyone except Pickles is outside than our plans will change. Because obviously it won't be Handsome that causes all the problems. We will be working on some sort of plan in case that happens.

Joe is otherwise a great person, I think maybe he just thought since I loved animals so much and already have to feed & clean, etc... them all that I could do the same for his. Which sure I don't mind feeding his dog, I have 3 dogs to feed at the same time anyways, that only takes a couple seconds of my time. But everything else I don't have time or sanity to do it all all the time. Like filling the cat food dish three times as often as I used to, cleaning more litterboxes and most importantly cleaning up the messes/destruction AND paying for it too.
Hopefully he sticks to his words! We shall see.