Hi Philip,
The first place to start would be to review the presentations from the conference on residency. You should be getting access to those soon. You can also review the basics here: https://internationalliving.com/country_clubs/costa-rica/visas-and-residency/ This will be a good refresher from the event.
The requirements for pensionado are pretty straightforward, mostly having to do with income. To apply though you’ll need to gather up several documents from home, like birth certificates and police records, and those documents will have to be apostilled in your home state or country.
That brings me to step 2. Contact an attorney and get the exact list of documents needed to apply. They’ll tell you exactly what to get and the procedure. Once you have all those documents you send them down and then you have to come down yourself to be fingerprinted and some other admin stuff that can only been done in person. Then you turn in your application and documents and wait for approval. It’s not necessary for you to be in-country during the approval process. But you can if you want, without having to leave the country every 90 days to renew your tourist visa.
Roger Petersen, who spoke at the event, is a great resource. You can find his contact info in your packet from the conference and at the link above.
Finally, just a personal note. I would encourage you to visit Costa Rica for several months first before you start the residency process. Come down and max out your three month tourist visa and really get to know the country and any communities you’re interested in living in. That way you can be sure you want to live here and that it has all that you’re looking for.