Is it because they could not fit Roosevelt in between the EXIT and the arrow?

Sounds like your half-sibling found other family members she relates to better. That's life. It's wonderful if you can be close to someone in your family, but it's not a given. If you need to spend some time with your half-sibling, call her up and ask to do something just the two of you instead of meeting at these gatherings with lots of other people around.

It sounds like you are on the fence. If you are on the fence, I would not do it. Maybe you are better off as a couple going to a place where you can watch other people do these sorts of things first and see if you like the idea of watching people and then maybe the idea of you being watched yourselves.

He shouldn't be using money on things like pistols. I wouldn't even let him in my house if he was unemployed and needed two pistols for some reason.

That aside, dude needs a tall glass of reality. You get whatever job you can, then you get choosy while you are earning money. I can't tell you how many people "hold out" for months or even years because they are looking for the perfect job. I wouldn't care what he was doing as long as he was doing something. Helping you out with no additional income and on his own terms is not going to cut it.