It was weird that a clone trooper would beg for money, while still wearing his armor. You'd think he'd have sold it, or it would have been stolen. It's as weird as seeing a Storm Trooper begging for money.
At this point in the timeline I think Bail it still trying to work for change within the government while seeing his options outside of it. Leia becoming a senator is more a family tradition thing, like Bail is a famous elected senator and he's expecting Leia to follow in his footsteps.
I think we last saw them at Padme's funeral? I don't imagine they know about the twins being alive, and I don't think anyone in canon has written a post ROTJ story about Luke and Leia going to Naboo to find them (though they should!)
Naboo's senate/queen thing is weird. I could be wrong but I don't think it's a traditional monarchy but two different titles. I think the 'elect' queens and senators are separate things (otherwise Palps and Jar Jar couldn't be senators).
Right I forgot the real take over happened in AHN. Makes sense.
The kids literally got sent to places nobody would think to look for them. Sending her to Padme's family would have been a real dumb move, especially considering that's Palpatine's homeworld.
No I just mean it's weird that:
1- The monarchy is seemingly abolished on Naboo, for no apparent reason at all, and that Padme had no family. What kind of queen was she to begin with then? Feels like it never made sense.
2- You'd think that AFTER the OT, Leia would have been known as who she really was, which is the daughter of Queen Padme, heir to the throne of Naboo. But because of #1 that was never a thing. Luke just disappeared, but in principle he would have been some sort of heir too. If LF originally wanted to GoT-ify SW (clearly why they hired D&D) that could have worked out.
3- It is weird that just as Queen Padme suddenly became a senator, princess Leia is expected to one day also be a senator, but I guess for whatever reason the Organa royal family are also politicians... like Padme was.