You seem to have the First-Timer, OverPlan, OverThink jitters. No cure but the first trip. Try not to lock yourself into a schedule pre-trip. Once you are on the ground, bounce around to see where/if any action is happening. First night in San Jose, I suggest Sportsmens, Taormina, Castillo but don't linger in any one of them longer than 1 hour if there is no action.
In Jaco, the only reliable action is the Cocal and even that is an evening scene. During the day, check out the main drag, especially Jaco Walk and the area around the Rolling Thunder Saloon. Then go to both Caritas and Malecon for a beer beachside. Don't expect to find action, just relax, have a few beers, enjoy the scene. Then clean up at your hotel and head to the Cocal around sunset.
When you return to San Jose, call Pension Monicas or Pension 360 to see if they are open. You will find their listings on Google Maps once you are on the ground. These would be the best daytime bets and the above mentioned hotels in the evening.
In the meantime, monitor the English language web sites QCostaRica and TicoTimes to get a feel for the local holiday atmosphere and events. I often came to CR during the holidays and never had a problem finding action during the dates of your trip.
_________________ If you lose your temper you’re phucking yourself - Garcia Marquez
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