I am all for giving up my US citizenship. Couldn't care less. My only concerns are for my pension and social security money. And....in my wife's case....her spousal SS income. I wouldn't want to take the chance of losing my US "money income". I don't plan on being any more than a "paper" US citizen.
Whoa! Again, that is a personal decision.
At the moment, the US tolerates dual citizenship. You can become a UK citizen without having to give up US citizenship. The UK also allows dual citizenship, so you can become British without a requirement to give up US citizenship.
I really can't think of any circumstance where citizenship becomes the determining factor for access to your "money income".
Several of us on this site are retired, are dual citizens, and have income sources from both countries. There are some on the BritishExpats site who are dual citizens currently living in the US and contemplating retirement in the UK with income sources from both countries. There are those on both sites who are dual citizens contemplating retirement with a plan to live part year in the UK and part year in the US.
It's an individual's decision, but one must cut their cloth according to their goals. Having to file a US tax return and a UK tax return is a complication most people in the world will not understand. Your goal may be to stay invested in the US, reap the largest financial rewards possible, and pay the least amount of tax possible to both countries (
and all that entails). Or, your goal may be to keep it as simple as possible, but with the knowledge that you may pay more tax overall (usually to the UK) but relieving yourself from the stress of the balancing act; allowing you to enjoy your retirement in the UK.
It's not easy, but it will only be as difficult as you wish it to be. There is no one correct way for everyone in this situation. The 'epiphany' is the moment you determine your goal and what is important to you. Your aptitude for dealing with the potential complications will determine whether you employ a tax accountant, or you feel confident enough to self-file. A professional will always strive to make sure you pay the least amount of tax, both accurately and legally, today as well as planning for the future. By self-filing, you may pay more tax (or maybe not); but it may be offset by not having to pay professional fees. The key is knowing where the tipping point is between the two.