I think the problem is money, cricket in West Indies isn't attracting a lot of money apart from the Caribbean premier league which started very recently, earlier cricketers were not paid a lot for playing cricket and also it's not that glamourous for you until you become a legend there. This might be one reason why there is no new talent coming in the team, also as West Indies isn't one single country so that makes the politics of the board quite confusing too, but I am very sure that this team isn't becoming a good team for next 10-15 years in Test, they are just going to struggle that's all.
Money were never been issue in Windies cricket because sometime back I read one statement from Board Member issue is not related to money they have some ethics issues which are now having some serious damage and sad thing is no one country able to have his own team so just because of this they are not having proper set up, but hopefully they will do some better in near future, or they will completely down and out like Zimbabwe because it's not going to stay like this for lone time. Right now they are having challenges from Afghanistan and Bangladesh as they are now on this level due to their personal issues.
Are you sure that money isn't an issue? As far as I know, WICB just earned around 116 crores last year and that also primarily came due to the Caribbean premier league otherwise they must have made even lesser than that, moreover, this number is just around what the Zimbabwe board earns every year which too is generally considered poor and always out of funds.
Who becomes the next PM of India we will only know in 2024. I do not support politics in sports but in my opinion, it will be not that easy to include Pakistani players in IPL in the coming years. Things are not that simple as it looks likes there are many within BCCI who do not want Pakistani players and remember IPL is still profitable and most watched without them.
Pakistan players were seen in early editions of IPL. I remember Shoaib Akhtar and Wasim Akram were there but things change for Pakistan after second or third addition of IPL, if I am not wrong. In sub continent politics control every aspect of the country. As long as Pakistani players are not missed in IPL, franchise owners won't include them.
I think politics control every aspect of the country in every country, it's not just about the sub continent or the Americas, Politics has always been a very key factor in the development of any sport in the country.