The benefit of the genetic testing might outweigh the cost if the only downside of testing is the insurance issue. As you know, there's a good chance that you'll have it since it is autosomal dominant.
From what I recall, the onset of myotonic dystrophy is early adulthood, and the symptoms usually start distally--i.e., with your hands. Thus, you might find yourself having to retire from practice before you pay off your student loans (which would be very hard to pay off in an alternative career, unless you could get public service loan forgiveness for working at a university). But the biggest risk, in my opinion, is that you could potentially find yourself in the financially CATASTROPHIC situation of starting dental school but being unable to graduate. In that case, you'd have hundreds of thousands of dollars of debt and no way to pay it off.
Yes, you're probably right (that's called an anticipation inheritance pattern, right?), but even mild dystrophy in your hands could be a problem. However, I obviously don't know enough to give specific advice.
Yes. But if you really prefer dentistry over medicine, maybe you should get the genetic testing before making that decision. There might be ways for you to get it done confidentially...genetic counselors may be sympathetic to the dilemma you're in.