What's with the pm hothead? The OP asked his question on an open forum. Is what you have to say so inflammatory you dare not say it here?
$200-225 a night will get a very nice place almost anywhere on the island he chooses. Yes, after fourteen years, there will be a little shock at the change.
Ruby's? Wtf? Not one third the money, more like 1/4 1/5. I'm not saying he shouldn't stay at Ruby's by with the budget set out, Ruby's hardly compares to a place in his budget. He should consider a place like Xanadu or maybe Mata Rocks. An ocean view at banana beach is much lower thsn his budget.
With fishing in mind, Scubaldy makes a good recommendation with El Pescador.