I always enjoy your postings...sorry I put an extra "o" in your name last time.
To answer your question, I was a sales agent for Pan Am for 10+ years, so did lots of traveling. Back 'in the day' it was mostly Europe or the Pacific. Now we like Central and South America, and (sob) we gotta pay a whole lot more!
I subscribe to Arthur Frommer's Budget Travel Magazine, also am on the net with them. If you are going with a buddy with the companies they suggest (Capricorn is a good one), it can be a great deal. With a couple, with a little planning, you can cut a much better deal on your own, so it depends on how you are traveling. I have a great need, as you may have noticed from my postings, to be at the place that strikes me most like what a country has been. Condos don't work for me. To each his own! If you take a package, they advertise the hotels they get the best deal with. Having said that, they will work with you on any hotel you want. I just checked with them re my pet, Paradise, this week. Need to call back, as I think I received faulty info, but if you find a hotel that strikes you as right, they will work with it. Problem is...its much more $$ than booking on your own. Most places on AC, given how slow it is there now, will negociate with you to a fare-thee-well. So, for me, I like to read the books (Lonely Planet is great), do some homework, and plot my own route. Lately, we've been lazy and just staying on AC...we've been all over the country, and now just dedicate our trips to diving. I find that is cheaper, if you check it out yourself. Dive masters included. So...that's my deal! We all have our prejudices, and that's mine!
My suggestion, do your homework and find a cozy nest that suits you. But DO the homework. Kills me to see someone hate our wonderful island because they put themselves in exactly the wrong place for their personalities. By the way, if you ever feel the need to go to South America, Escapes Unlimited is wonderful. They, too, will let you mush around with what you want. We had a great trip to Peru a couple years ago. Just ask for what you want whatever agency you speak to.
Take care, M