A lot of questions, but I will try to help.
1. Traveling solo is fine. Just be careful at night in more sketchy areas. English is pretty much everywhere from a business perspective in Jaco and in many places (if not all) in and around San Jose. The girl's English will be hit or miss - but with translation apps it makes it workable. Overall I am never worried too much, but always keep an eye open. In Jaco you will find friends and people to hang with. Go maybe to Oz first to get a drink and then walk into the world of the Frog Bar at Cocal.
2. Not sure of many deals. I tend to book direct with things and have found places that I like - Hotel Jaco, etc. I have not stayed at the places you are looking at. I like Jaco better just for the beach and the numbers of women and playing in a "safe area". San Jose is surely cheaper but a bit more spread out and it feels a little more dangerous. Not sure it is, but just has a feeling of it.
3. Have not stayed at either. i would say no on the Best Western from what I remember. It has a new casino near it, but still think it may not allow unregistered guests. That is the big thing you need to ask. Do they accept non registered guests into the facility with you. I know the Marriott Los Suenos does not as I have been chased by security there once. Really funny...
4. Raining season is cheaper. A little less women (some from Venezuela and Columbia may have gone back home) but still a lot. I like the rainy season personally. I will say there are floods and there are landslides so just be open to maybe slow driving and some water. Overall it just usually rains a little in the early morning and then again around 5pm to 7 pm maybe. Not horrible usually.
5. I am not a fly-fisher, but I love off shore fishing. While not cheap, look at Maverick in Los Suenos. They actually build their own mult-million dollar fishing boats and have a great excursion.
On the travel package, I just usually do not play that type of game. They tend to get you into planned activities and you do not get to do a lot of self exploration. I like to go to a country and learn while I am there. Maybe I waste some time, but I get to know more...
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