Hi Ken,
Some thoughts...
I am passionate about timber framing on several levels; to build my own house and for greater historical projects.
First of all, TF is still seen as a artsy-craftsy curiosity by many home owners who also have limited pocketbooks, especially now. Many people like the craft, but its not a cheap approach so this does limit who can afford it.
Second, its hard work. At 37 years old, I hate saying this but I feel many young(er) people are lured by the information technology/computer arena (or other fields that pay very good money for less work)...so this tends to reduce your pool of contestants. I dont see this as a huge problem in some ways because TF is still regaining acceptance. It would be far worse if there were tens of thousands of TFramers who were out of work.
Proximity. While I am self taught at many historical trades (blacksmithing, armouring, period wood work, etc) I find that timber framing is a much harder craft to practically experiment with due to its inherent size and related costs. I have tried to read as much as I can, and have acquired many period tools in an effort to learn TFing but its hard to find big logs that one can surreptitiously 'work' in ones backyard without alienating neighbors
So before the economy took a dive, I have hunted around for local framing business in the mid-Atlantic/Washington DC area. Few framers (that I knew of) exist out here near Washington. And of those that did, I did not get a sense that apprenticeships were ripe for the taking. Maybe I was wrong, however open slots for "seasoned newbies" was still not prevalent. And professional training can be hard if one is married and has a family that depends on a certain dollar income to survive; a poignant fact particularly now.
While I am self employed, and earn a fair living, I would jump at the chance to apprentice with a TF company if I could bring down at least 35k (to pay the mortgage, bills, etc and somehow manage to see my family a few times a month during the duration of the apprenticeship).