The way I see it is:

Corporations and Individualists are unlikely to try for getting land in space unless the claim laws change.

Governments are unlikely to change the claim laws because of all the disadvantages they would face for doing so.

So until this becomes changed there isn't going to be a lot of individualist oriented exploration/claiming of space.

As for region by region analysis, perhaps my view is biased, but I don't think the governments to which you refer are the most likely candidates for space exploration, so concentrating on governance in countries with actual Space Programs would suggest my 500 year claim is valid. As far as it goes with democracy, if change isn't occurring its because people aren't making it happen. This isn't as easy as it sounds but its certainly possible in a democracy, in a monarchy the main methods of policy changes were executions and civil wars.