generally, if you're "starting out" you aren't already wealthy. that's basically the whole concept of "starting out".
and yes, if you sell the property for a lump sum, you can pay off a bunch of debts at once - but then you no longer have the income-producing property and the one-shot windfall is likely less than the value it would produce over the rest of his lifetime. that's the difference between immediate and delayed gratification.
I'm not addressing the rest of your post because it's stupid.