Based on the information that I'd previously described, I sent an email to the Logbook of The World (LoTW) desk at the ARRL in mid-June briefly explaining what I'd learned and asking what would be needed for them to issue a certificate so that I could upload my contacts. (Briefly, each contact is "signed" using a digital certificate to ensure that it's valid. The ARRL issues a certificate to an operator when it is satisfied that the contacts were made legally.) I got a quick response back which referred me to the ARRL's Reciprocal Operating page which gives the requirements needed to operate from different locations around the world. The information provided for that page links to OH2MCN's terrific site that has details for hundreds of countries. The information on his site is largely provided by hams who have operated from those locations, but sometimes it's not always completely up to date. (As an example, you can see my contribution to the entry for the Cayman Islands, which in turn has been updated since I wrote to Veke.) Unfortunately, the information for Costa Rica did not include the updated details regarding SUTEL (and still doesn't as of the time that I'm writing this.) I responded back to both the LoTW desk and the DXCC desk (since the DXCC desk is ultimately responsible for determining if an operation is "legal"), but did not hear back from them prior to leaving for Costa Rica.
After I returned, I electronically requested a certificate for my operation. As with most operations from other that a home country, I was advised that I needed to contact the ARRL with the required supporting documentation. I sent another note to the DXCC desk in early August again explaining the situation but after a couple of weeks of no response, I sent a note to Joyce, KA2ANF, my Division Director who did whatever magic Division Directors do and got me a reply form the DXCC desk. Unfortunately, the reply was substantially the same as the initial responses that I'd gotten back (referring me to the Reciprocal Operation page) and didn't address the changes in the licensing authority. It said that even though their information was outdated, that I'd need a license or some other documentation from the local licensing authority.
At this point, it occurred to me that many of the people who I'd emailed or spoken to had operated recently from Costa Rica, certainly within the last two years, and several had been issued LoTW certificates. Since there was precedent, I figured that the best way to find out how they had gotten their certificates was to ask, so I gathered up a list of email addresses, and sent out an email, that said in part:
...I noticed that you have recently uploaded contacts from a Costa Rica operation to LoTW, and I was wondering if you'd recently obtained a certificate without a paper license, or if you had a previously-issued license that was used to obtain your certificate. To be honest, I'm hoping that you might fall into the first category meaning that there is precedent for my certificate to be issued under the same conditions.Over the next couple of days, I got back responses from pretty much everyone I wrote to (and some that I didn't; my note got passed on to a few others who I hadn't originally written) and the story from each of them was the same: No, SUTEL wasn't issuing licenses but it was OK to operate from Costa Rica as long as you were in the country legally and had an appropriate US license. N0KE, AA8HH, N0SXX, and K4VAC (which is a club) all confirmed that they'd been issued LoTW certificates based on the "new" information about licensing. Better still, I received information from several hams that included emails between themselves, the ARRL, and in some cases, between Keko, TI5KD, the president of the Radio Club de Costa Rica where the licensing information was explained and accepted as valid by the ARRL.
I wrote another note to the DXCC desk and provided this information, and waited. After another couple of weeks, I sent a reminder note (I know those guys are busy, and my issue certainly wasn't a big one) and got a response back. They'd started to investigate, and would be getting back to me. I felt that at least they were finally reading what I'd written and there was hope. Just a few hours later, and I got back another email telling me that my operation was accepted and a LoTW certificate would be issued shortly. (It was.)
I'd like to thank everyone that I mentioned here for their help in getting through all this. In particular, Keko, TI5KD was very patient in explaining the situation and helping me to be confident that I would eventually get through the red tape.
On a final note, I realized that in the spirit of "giving back" to the ham community, the best thing that I could do would be to get the information on OH2MCN's site updated, so I'll be writing to him shortly with the details that I've provided here (though in a more concise form).