DSL service was problem-free both places I've had it connected. With Verizon they turned it up before the due date. Couldn't have been easier both times.
No experience with dry loop DSL but I suspect the telcos aren't that thrilled about providing it even if landline voice service isn't the cash cow it once was, and it may be a weird service order to type up for the representative, which means mistakes are more likely and it could get passed off to someone else to type, providing more potential for service order accuracy to be compromised and to create issues down the line. Trust me. I've worked in the thick of such environments for Ma Bell.
Ralph