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1. Medications: Lot's of info on blue diamonds and vitamin C out there. If I want/need to get stuff like asthma medications is that doable without much difficulty? Any issue coming back to the USA with non narcotic prescriptions obtained in CR?
You can buy most meds in CR without a prescription. Only the addicting narcotics (Schedule II and III drugs in US) are hard to get without a script. Bringing meds back to US is not as big problem. There are laws in place for how much you can bring back with, and without a script. Do a search online.
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2. Color copy of passport, entry stamp, etc: Recommendations on places to get this done? Do I need to find a copy shop?
I used to get the laminated credit card sized copy of the bio page and entry stamp. But in over 60 trips, I have only been asked to produce ID once at Bar Idem during an immigration check. So lately, I just ask hotel reception to make me a black and white copy of the bio page and the entry stamp. I trim it nicely and fold it up and stick it deep in my wallet so it won't get wet/damaged. But I speak Spanish, so I could talk my way out of a sitaution where that wasn't good enough. If you're new, a color copy is probably a good idea. The copy shop BangBang mentioned on Ave Central is good. I posted a picture of it on the VIP photo gallery. Search for "copy shop" in the gallery search box or follow this link:
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3. Calle 6: I must admit a degree of intrigue by the seediness/bargain hunt factor of these salas. Much of the reading on this area suggests one should fear for their life. I need some perspective though. Assume a mid-day visit: solo, sober, no flashy jewerly, limited cash etc. Estimated probability of a gringo returning to home base unharmed? Not counting one being relived of leche and the cost of a session.
Unless you are working with a small budget, I would not waste my time with Calle 6. Safety-wise, no biggie during the day, just be smart. You already know to leave the jewelry, watches, expensive cell, at home. Take the advice to go with a wingman the first time. You don't want to be seen lost or wondering around aimlessly.
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4. Molino Rojo: Another intriguing establishment. From my research it sounds as if it had its heyday years ago. I did see a couple reports from late 2013, any updates? One can session on site, yes?
This place sucks. I honestly don't know anybody who goes there. This place is completely dark, you can't see how the women look, even standing right in front of them. Mostly fatties. The "rooms" onsite are pretty dingy, and hot.
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5. Bus system within San Jose: Anybody using these? Worth the effort during the day or no? I see lots on getting to other parts of CR using buses. Less so about traveling within the city.
Taxis are cheap and quick. It would take you a month to learn where the buses go and where to catch them.