OP: I'm in the same economic range as the one you describe, and indeed things do change! When I started living this way nearly ten years ago it was Brazil for me, and now that country is not on my map; not only is the exchange rate half of what it was, but prices have (at least) doubled, which right there makes it four times what they were. Two examples: in 2001 a ticket for the subway in Rio was app. 20 US cents, and is now well over a dollar. I stayed in a small vacation town and had a nice little cabin for US$8, the high-roller place in that town was US$35. A few months I ago I happened upon the web site of the expensive place, and it was over US$120.
Something you will have to contend with if you spend time in Colombia is the reception that Immigration/Customs/Homeland Security et al will give when you make a trip to the US. Expect a lot of suspicious questions, having your bags thoroughly searched, and so on. You may not have anything to hide, but having to deal with this all the time can be wearying. Same can be expected returning from SE Asia, expect to have all your electronic data inspected (camera, computer, memory cards, etc) and know that a having something as benign as a bare-assed picture of your infant nephew on an bearskin rug may alter your future plans severely. I've lived a while in SE Asia and thankfully none of these things have happened to me, but I've heard of enough incidents.
Another is the assumptions people will draw, based on some tawdry article they picked up somewhere, and they'll project their fantasies on you. I had one friend whose wife would give me this smug and disdainful “I know what you're doing over there!” attitude. Well, when you're someone's house guest you can't say “f___ you and your assumptions, lady,” and then again this is the kind of thing where the accusation itself is a condemnation (re the tactic Nixon used against Ed Muskie in 1972).
This is all stupid stuff, but be prepared for it when it comes your way.