He might say something like, "you work with the lot in life you are given," but not go into the verbose exposition I've grown to expect from philosophers of the Age of Reason.
Well, yes, he's turning the things he got from his teachers into aphorisms and rephrasing them to keep them fresh in his head without turning them into words to be repeated out of habit. It was his journal and not meant to be read by other people; he didn't need to explain things to himself at length, just to remind himself. If you want a lengthier explanation, Epictetus is one of his student's notes from his lectures, and is meant to be instructive, and Seneca is as verbose as anyone could ask for. None of them are up to modern standards, because even philosophy has made some progress over the past 2000 years, but there are books that are meant to do what you wanted Meditations to do. Meditations just one of them. But do read Pierre Hadot's The Inner Citadel for why Meditations isn't as shallow as it looks.
It has certainly changed considerably, at least. For the Greeks and Romans, philosophy was expected to guide one in how to live one's daily life. That role is mostly expected to be filled by religion nowadays, not by philosophy.it's actually possible philosophy has gone backward in the last 2000 years
Hadot agrees with you. I don't think I do. We've gained precision, and the cost of that is that we know when we're waving our hands. It turns out when you're talking about big things like how people in general ought to live, you invariably wave your hands a lot. It makes attempts to talk about them look ridiculous, and trying to talk about them feel ridiculous. But the ancients were waving their hands too, they just didn't know it.
The greatest hand-waver of them all was dear Bertrand, though. I always secretly pretended he was Bertie Wooster's namesake. In all seriousness, I tried to articulate what I disagree with here and I can't, really. Just that I've read a lot of post-Renaissance philosophy and a lot of classical philosophy and a bare handful in between and I know which era I'd pick if I was on a desert island. If that's the best rationalization I can mount, though, I clearly don't belong with Descartes anyway.