First, welcome to the board.
Why Jaco? Is it for the beach? The beach sucks and the water is polluted and smells bad. You will be kicking yourselves in the ass for wasting 5 days in Jaco and only booking 2 days in SJ. I'd say go 2 days in Jaco then 5 in SJ. If you don't, please come back and tell us all about Jaco.
The condo thing shouldn't be a problem for most girls. I know from experience that there are girls in SJ that only go to hotels, but it's a very small percentage. There may be a few in Jaco too. I wouldn't worry about it though.
As long as you carry a photocopy of your passport bio page and the page with the entry stamp, you shouldn't care any less about any raids. It's not like you are an illegal hiding from immigration. Show them your papers and they can kiss your ass.
You will have a good time, but use your head. Read this post first, it may save your life.

Well, maybe not, but it will give you a lot of info about different aspects of your trip:
https://costaricaticas.com/phpBB2/viewtopic.php?t=16357