I'm confused over what exactly $$$ means.

Please help $ - ??? / $$ - ??? / $$$ - ???

A recent review stated that he gave her another $$$.  The services described did not warrant much over $100.

$=100, $$=200, $$$=300, and so on.

$ = 100
$$ = 200
$$.5= 250
$$$ = 300
and so on.

I think occasionally people don't follow this convention.

Now that my dear is a GOOD LOOK!!!!!!! $$$$$$$$$$$

Or, more likely, the review when submitted had the specific amount, and TER substituted the $$$ for the numbers.  You are not allowed to mention specific amounts in the details.  (but yet, you have to put that in the form you fill out - makes no sense to me but then its their rules)

This happened to me once.