I've just noticed (After playing for 3 years xD) that if you start the Speed skill run and die the timer continues to run, I'd suggest a fail on death feature (Because you'll probably'll fail anyway), that way when you get back you can start anew
Update: I started one 18 hours or so ago with D. Holliday, timer never timed out...
I'm John H., Tom Foolery, Dresden (not German), King Fisher, Clay, John Frost and Preacher.
Now if you die after starting the run, and return to Miriam to restart, she automatically gives you the Speed Skill without your ever having to talk to Pachua or complete the run.