Originally Posted by MikeFromTokyo

It is not a matter of possibly having to pay an additional fee for award bookings. It is VERY unlikely that any Virtuoso agent will be interested in handling your award bookings.

As hotel bookings are typically cancelable and changeable it is not in fact usually necessary for flight and hotel bookings to be made exactly at the same time.

Agents might be deterred if you approach them with a long list of requests, especially if the amount of expected hotel spend is not particularly high.