Would it be safe to reuest both, or does one risk having to pay double, both points and money, for the same upgrade?
Optiontown allows SK an additional revenue stream where a flight is oversold in a certain lower cabin class. The customer pays to be at the front of the op-up queue. Upgrades with miles are an additional revenue stream where a flight is undersold in a certain higher cabin class.
The only overlap would be in the case of oversold lower cabin class, undersold premium classes. In this case I would assume Optiontown to take preference as the revenue generated to SK is clearly significantly higher. I doubt there will be much risk that one pays double for the same upgrade. These op-ups are manually handled by revenue management and they would have a certain order of priority.
(Of course this is from my armchair CEO position. Who knows what SK would do)