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I have asked this question

Obtain insulin in Colombia as a foreign tourist

In fact, after visiting Colombia I'll be travelling through 8 other countries in Central America and I'll want to ask the same question for all of them.

I'm unsure as to what I should do - I could include the list of countries in my existing question, or I could repeat the question for each location, changing nothing but the location names. The former seems to make the question ridiculously broad, to expect an answer to cover every single country, but the latter seems too redundant and breaks up very similar information across the site. Two sides of the same coin really and I'm not sure either option is particularly good.

However, I do need an answer for each country I'll visit and whilst the question is identical for each country, the answers for each could and likely will be different.

I'm new to the site and have the feeling this scenario must have come up before, though I can't find a similar question on meta.

What's the done thing here to segment a question and its answers by country?

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    Since one thing we like to see in a question is initial research, a worthy question might be How can I find out how to obtain insulin in a particular country? rather than specifying the countries. – choster Mar 9 '15 at 23:07
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For you, yes, it's a little hassle, but the advantage is that if you have:

"How do I get insulin in countryx" for 9 different versions of 9, is that it'll benefit future users.

People will search for 'how do I get insulin in countryy' and your title being an exact match is much more likely to come up. At least in my understanding.

Aside from the SEO and search benefits, the problem with asking it in 1 question is it's likely too broad. We often close questions like that because you run the risk of nobody knowing the answer for all 9, or some people posting answers for 1 or 2. Which doesn't satisfy your entire question, but now it's been marked as answered. Which sucks for you and future users.

And as someone else pointed out, rules may differ in each countries, so a single question may require an essay to answer 9 different sets.

So split them up, I say :)

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I would ask them in separate questions, but at different times so it does not give an ugly look to the main page of Travel.SE and to make them more acceptable.

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    plus, you can see how people edit or react to your first question and adapt the others in consequence. – Vince Mar 8 '15 at 16:27
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Different countries have different rules, so those are seperate questions.

Unless, of course, the same answer applies to both (that is, the anwer is based on the same regulation that can be quote, for example).

But if both countries have only similar, but distinct legal regulations, those are still different questions because a good (documented) answer will quote other regulations.

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