I don't live in Costa Rica, still have various obligations and need to be in the USA for the time being. However, I have been coming down to CR for many years now. The main things that I have noticed about the attitude here is the lack of promptness, the lack of desire to do more than a mediocre job, the "that's the way it is here" attitude, the general lack of planning for the future, and the "that would never work here because..." attitude.
I should state very clearly here that I am not only talking about Ticos. Gringos and indeed the majority of foreigners here seem to develop the same attitude very quickly. "That's the way it has always been done" is the general answer when you bring up a new concept. I have always been the kind of guy that looks for opportunity, and I have seen many unexploited business models that are commonplace throughout the world. But very few people ever challenge the status quo in CR.
The first couple of years I visited here, I generally trusted the people that I came to know and believe were level headed. However, there was still that prevalent attitude of "that just won't work in CR" with nothing other than strictly anecdotal evidence. After that first couple of years, I started to spread my wings and challenge that notion. I have been right up in the face of several Ticos and Gringos challenging them to take a dare (in a generally friendly-but-serious wager kind of way) that things can be done in CR that everyone says cannot. I only remember one or two people actually agreeing with me. The rest were pretty much convinced that I was crazy.
I am in no way bitter or angry about that. In fact, I have encouraged several people to continue to spread the rumor that I am a "Loco". Please tell everyone. My short trips to CR are far more profitable because I quite literally have zero competition. I have several ad-hoc businesses going, none of which are illegal, that are successful simply because everyone else believes "it can't be done in CR." I make more than enough money to pay for an entire 5-day trip -- including airfare , hotel, bar, food, and entertainment -- in the first day of my visit, or at the very worst, a couple hours of another day. And I am talking about over 100 visits, every time, without putting forth that much effort (I am, after all, here to party).
The very few people that I have met that have also noticed this paradox of CR culture have also done quite well. They also tell me stories of Ticos and Gringos who constantly remind them how "Loco" they are. I used to try to get others involved, primarily to get a business running steadily while I was in the USA, but the lack of belief and interest pretty much convinced me that I was wasting my time.
At any rate, as I mentioned above, the lack of interest and belief is a good thing, so instead of soliciting for help, I am pretty much keeping what I do and how I do it a secret. The benefits of no competition vs. pounding my head against the wall trying to convince others to think outside the box have convinced me I am headed down the right road. I can't wait to finish up some loose ends in the States and head down to CR in a couple of years. Should be able to work about 10 hours a week and live very nicely, keeping the retirement money available for my un-scholarship-able K*ds to get some Grade-A letterheads on their degrees.
So I leave you all with this thought: I am not trying to rub anything in or brag. I am just trying to say that all of this "That's the way it is here" is quite often rubbish. You might have to get innovative and attack problems from a different angle, but there are so many unexploited LEGAL opportunities in CR that you should be able to find something that you enjoy doing and make a killing at it.
Peace.
Baseball season is on the move, BTW

Pretty interesting response. You say you have five businesses that are legal that support your trip to CR. Would you care to elaborate? Lot's of people who live and travel to Costa Rica are looking for various revenue streams.