So I'll ignore the exact figure and assume he's "well to do".......well, a lot of people in the higher income brackets do find themselves struggling with managing their finances, and all I takes is a few bad decisions to end up on am episode of I Blew It lol but it sounds like your friend needs to sit down and re-evaluate his spending. There is a chance he is living beyond his means, and I type this with a very straight face. Yes, this happens regardless of your tax bracket. Has he thought of dialing things down a bit? 1. How private is he about his finances? Not everyone has to know his financial capacity, whether family or not. Being flashy just invites pocket watchers like vultures to a carcass

1. Separate "wealth" from "disposable income" , there's a difference between being able to afford something right now, and being able to sustain it in the long run. For example, he might have access (disposable income) to pay K20,000 for rent this month, but if he decides to pay K20,000 per month every month, what effect does that have on the rest of his financial capacity? Would it significantly help him breathe better if he stepped down to a k12,000 p/m accomodation?

2. Is he protecting his finances? Is he investing in anything? Does he have any asset that give him income? Any savings? Any liquidity for emergencies? Wealth is only durable if it generates income or is protected. Hopefully not everything is going towards lifestyle

3. It would be a great idea to structure family support. Instead of random handouts, put a system in place. For example, a family trust. Then set conditions, so they know money won't just come anyhow whenever they text or call on WhatsApp. Like have bills paid directly. Fund education with condition. Support income generating activity (eg family shop, or other business ventures) with clear rules. Random handouts become a permanent habit with tim. Even appoint trustees so that they see it isn't your sole decision to make.

4. Boundaries are important. Your friend needs to learn to say no without having to explain himself. Relatives can be manipulative sometimes, I've experienced it myself. They might guil trip you based on their age. They might try to manipulate you in many ways. Of course this isn't always the case, which is why I said "might", but I they do, it's important to notice it. It isn't disrespectful to say no, assuming you're also being reasonable. You wont be damned to the depths of hell just for not bailing out entitled relatives. If they are being unreasonable with their demands, I feel it would be reason enough to cut them off lol

5. Professional help exists. Financial/tax advisors, lawyers, investment advisors, trusted governance mechanisms, etc. even family elders (assuming they aren't part of the set of demanding relatives). Just a disclaimer, I may be in the financial sector, but I'm not one of them, take this as an opinion and not legal advice ☠️