Puerto Rico Bound!

[RolandofEld]

Greetings, newbie member here, first post so be gentle and all that.

Anyway, I figured I'd consult with some experts as to what I should do about an upcoming vacation at a friend's place in San Juan with regards to cigars. Maybe you can help me out.

My background: I'm a rookie cigar aficionado of the most casual variety. After researching things a while back I bought a box of maduros to enjoy during the week leading in and week after my wedding almost a year ago and really enjoyed them. I've eased off them since then and still have some left in the humidor. My smoking habits are to slowly enjoy one when company is around that would enjoy one or brought a few themselves to share. Probably once a month or so when I'm not on vacation.

My taste: I can smoke for about an hour without losing interest. I liked the maduros that my local cigar shop owner pointed me towards. I can't recall the brand/make/size off the top of my head but they were of average size and shape and in the same price range as H Upmans or so. Maybe robusto size? Not pyramid or torpedo profile. My cutter is a xikar that has been a pleasure to use compared to the crappy double guillotine I see others using. Well worth it.

My situation: Since I'll be on vacation for a week+, and I may be sharing a few with friends while I'm there I'm looking into if it'd be better to take some with me or to just buy some when I get there. I have no idea about the market or the availability of cigars there. Please note, I am not trying to make this thread about cuban cigars and/or procuring them. I'm not sure I'd have the palate to appreciate them and I'm not down for dealing with sellers claiming to have X but is really Y and on and on and on.

My questions:
1) Would it be better to take a handful of cigars down there with me or to seek out a vendor while I'm there?
2) If I can get good cigars there at a reasonable (or even excellent!) price where should I go to procure them? We'll be basing our travels out of my friend's family home in San Juan (near old San Juan I think) so bonus points for finding something there that isn't far out of the way or a travel inconvenience to the group of friends I'll be traveling with. We will be traveling a fair bit so other locations are fine as well, just maybe more random in nature.
3) Any tips for traveling with cigars would be appreciated. If I do decide to travel with some I was just going to pack them into a ziplock inside a ziplock with the moisture device shoved in there as well. That, some extra propelyne glycol, a zippo, and my cutter would go into the checked bag for the flight over. I'll have to check on that zippo but it shouldn't be an issue in the checked bag I think....

I saw the following thread (as well as a few others) related to Puerto Rico and didn't see any of this stuff addressed specifically so forgive me if I missed this being brought up already. I did try to search first.

Bonus points, aside, and maybe I should just make another thread... Anyway, I tried to search this but didn't see anything obvious and got a high noise to signal ratio with my search. I'm looking at making a leather cigar case in this style. I've got some veg tan leather hides that I got from a Tandy leather store and all the tools I'll likely need. I'm currently attempting to mold some of the cut pieces into a workable shape but a nice DIY guide would be great.

Thanks for the help!