Not necessarily. Your first post mention economy class. The answer may be different if you are looking for a premium cabin, because the relationship between ticket prices and award ticket mileage requirements is different.
+1
The chance of scoring a premium class seat (or I should say any seats at all) with UR depends highly on the traveler's flexibility and the number of people travelers.
For example, in OP's case, even the award inventory may not be available yet, OP's foreseeable problem is not about getting to OGG, but leaving from BDL. OP's best bet will be leaving from EWR or BOS, a less than preferred alternative.