Hi Rmwik,
We’ve stayed on both sides of the Osa and liked them equally. I guess it really depends on the type of experience you want. Drake Bay is still a really small village, but there are restaurants there and it’s easy to arrange activities. Bosque del Cabo Lodge is much more remote since it’s well south of Puerto Jimenez (the nearest town). There will be things to do there but not a lot going on outside the lodge. As for flights, you would definitely be fine with an early morning small plane flight out of Drake. Just time it so you arrive 1.5-2 hrs. before your international flight. The airport in Puerto Jimenez is a little farther from Bosque del Cabo on a rough dirt road, but you should be fine for that too as long as the flight is early enough. Just allow a little extra cushion for the drive just in case. The weather shouldn’t be an issue either way since it’s usually very dry and calm in February.