Thanks for all the helpful replies.
First, I thought I should clarify a few things. I am not necessarily interested in being a perpetual tourist, unless choosing to live in CR for 2-3 years makes me a "tourist." I speak conversational spanish, am interested in learning Tico culture, customs, making Tico friends, etc. As I mentioned, I am a very experienced traveler (differentiating from a tourist, in my mind). As much as I would love a due diligence trip to see if I would like it, this isn't really financially feasible, and frankly I am not sure it's necessary. I have lived quite happily in many countries with far less developed economies and quality of life than what I hear and read of CR (from friends who have actually visited / lived there). My plan is already to bring no more than a couple suitcases and store everything else.
I am slightly confused by the residency programs though. With my internet business, I make almost 2500 / month. I DON'T have a 150,000 to deposit into a bank at one time, and I'm not sure it can be "guaranteed" (beyond showing past history). Does this disqualify me for residency? If so, it wouldn't be a huge hassle for me to do a border run every 90 days (I did this in Thailand every month for 6 months), but I read somewhere that you can only do this once in CR before being barred for 6 months. Is this true? Or is it just hit or miss? I'm not trying to "game the system" or anything like that, just live and work for 2-3 years (I know I can't get a CR job). I would happily apply for residency if that would enable me to live for that period completely above board, but I'm not sure that my status qualifies me or not.
Thanks for all the helpful feedback!