Have a slight concern. I have a 92' 2.3L with the M50DR1 trans, when it is colder out it is hard to get it into 2nd gear until it warms up. Is this a common problem or is it just me? I have replaced the fluid about 5k miles ago with Mercon V, and I plan on doing another fluid change in a few weeks. The clutch has 18k miles on it, but the master and slave cylinder are still factory at 110k. I did change the clutch fluid, the system is bled properly as well.

 

The slave should ALWAYS be changed when doing the clutch. It's one of the highest failure rate components in the truck.
A previous owner may have also thought it just fine to always start out in second gear. This puts undue wear on the syncros in the transmission.
Or it could just be the rpms you're shifting at.