Hey Lee -- just some general comments, nothing worth PMing about.
We were looking for awhile to go on holiday to Venezuela, ultimately we aren't going to just because it seemed like a bit of a pain in the a%$.
There's a huge black market for dollars and everyone pretty much uses it. Government rate = 2:1, black market rate 4:1 for the USD:Bolivar.
My friend's wife is Venezuelan, when we said we were going to go on holiday she just laughed at us, then said, well, there's some nice places but bring TONNES of cash because most places don't do credit cards or debit, and if you try to take cash out of the machine you'll be charged government rate.
My husband's company is sick of the bureaucratic headache of Venezuela so they are pulling everyone out by December and their just leaving skeleton staff. He is good friends with one of the Venezuelan guys and he's always laughing at Argentines that think doing tramites here is a pain in the butt -- he says you have no idea just how much more of a headache it is there.
Now in terms of living there, Caracas is supposedly a shithole compared to BA -- I haven't been personally so can't tell you firsthand. Las Roques is a place that everyone should visit once in their life, but in terms of living, it would be pretty rustico. Isla Margarita is supposed to be full of fat American retirees / surfers and kind of boring -- besides the thing that would drive me nuts with Margarita is that it's a tourist island, and any time you want to get away you have to fly, there's not a lot of places to escape to that are nearby.
Most expats are based on Margarita, Las Roques and some of the other islands are full of Italians -- not a lot of Venezuelans want to hang around -- if they have the money, they get out of their own country it seems! Cost of living supposedly relatively high (being an island and all) -- when I looked into going 5 years ago there was only dial-up internet, I am assuming that has changed by now, but internet in Venezuela not supposed to be great.
My vote would be for Colombia.
However we're going to Panama in a couple of weeks on holiday, and it's kind of becoming the next CR for retiring expats, so there's a tonne of info on the web -- seems like it's pretty easy to get residency and they have good benefit packages etc, and real estate is still pretty cheap. There's a lot of areas that are just being developed, and the nice thing with Panama is that it's tiny, so even if you don't live in the Capital, you're only a few hours drive there. We're going there because of the time of year for our trip -- it's rainy/hurricane season in most places, whereas Panama maintains a fairly steady climate all year round so we can do a decent trip of city / fishing / snorkel / beach / jungle / rafting / shopping for cheap electronics in a relatively short time. If you want when we get back from the trip I can drop you a line and let you know whether I felt it's a thumbs up or thumbs down! Of course travelling and living are pretty different.
You two should book a trip Venezuela - Colombia - Panama and get a feel for the places before you pack up... late november/december would be a good time to go and usually if you book in advance you can get flights to Caracas for as little as 500usd (Caracas is much cheaper to fly into than Cartagena, but traveling overland into Colombia can be a little complicated)