1. Tree structure for countries - mainly for various "States", but affecting many more
2. Advanced search on country list page + Sorting by different criteria
3. Creating "secondary" lists (for example for micronations) - easiest step
4. As many countries overlap, they could be shown at different places at once. For example, Spanish Netherlands would be foundable under both Netherlands and Belgium.
As a result, there would be quite a lot of new countries that would count as such. You can open German States to get some hint about how many.
I cannot really give you any timetable, as there is not any, we are currently in preparatory phase. By preparing, we would like to make sure everything will work as intended and that there are no flaws in theory. Everything above stated is thus work-in-progress and may change.
Once we discuss it more, there will be some looooong informative and feedback wanting thread. But feel free to ask and discuss here, as any input would be great.
It seems that maybe this subject should be addressed under a new topic so that it reaches a larger audience. I'm sure that there will be immense interest in this topic.
If states from each country such as Austria, Germany, Italy, Islamic, Indian, etc. count as new countries, we will have to have a 500 or 600 country club.