A few things.
I actually don't think that Myers Leonard contract is that bad. I think next season will be telling for him, he should produce just fine when given more minutes. Stretch 5s are the future and he could end up being a steal.
New Orleans didn't have any choice but to bring back Jrue Holiday. They were allowed to go over the cap to keep him, they wouldn't have had the room for a Teague or George Hill.
If they just let him walk that's essentially forcing Boogie out and would make AD force his way to Boston or something.
I'd be horrible. My style would be to try and avoid big countracts for all non-superstars unless we were a contender. Otherwise It's easy to sit back and never want to do that but not many owners cool with being bad. So they'll pressure you to sign somebody to show progress which is how the shytty contracts end up happening. I'd want to just sit back in free agency and hope for the bargain signs and be fired in like two years.