^ Thanks Brent, but the joke's on me. MA bureaucracy wins again. Turns out that the agent I scheduled an appointment with (over a month ago) is only able to help seniors get health insurance. Even though I might look like one, I am in fact not a senior. This tidbit of information would have been handy to know, but none of the people on the other end of the half dozen phone conversations I had every saw fit to point it out to me. I am back to square one (well, square two, I've got all the sodding paperwork in order on my end) and once again am diving face first into the slow, churning gears of the Taxachusetts bureaucracy. This should be a hoot.
Fun side note: The agent I met with had the first name of Tyll, pronounced "Till." He's of Dutch descent and named after a folk figure. He's something of an amateur photographer, having shot both 35mm and 120mm with Rollei. I did not learn his position on headphones or motorbikes.