Personally, I would decide what is affordable as spending money from my investments based on a "safe withdrawal rate" of about 3% per annum. There are lots of published articles on the subject.
Calculating that what's affordable based on the returns from one very good trade seems much more risky, as there are big falls as well as big rises, so some kind of long term view could be safer.
Anyway, I suspect Rocket may have that worked out too and we're at risk of offering too much "advice" here.
Incidentally, if the lad is still working as a money boy, I presume he would offer his services to anyone else for the going rate without asking for $500 a month. So just as soon as he realises Rocket is standing his ground at $200, I imagine the lad would accept that.
It's a good offer and $200 a month more than I would consider.
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I won't be offering any more unless he asks for it. I've already given my advice. It's pointless to offer advice to someone when he obviously has no intention of taking it.
There's a very fine line that separates "Love" from "Obsession". So fine in fact, that it's completely transparent to the naked eye.