Handcuffs

By some quirk, I only have one catcher after the autodraft. If I made no changes to my roster, I assume the game engine would allow me to continue with an illegal roster. However, I do need to add/drop some players during waivers. So my question is this - will I need to pick up a second C first - before I can make any other waiver moves? Thanks.

Are you sure you don't have a 2nd player with catcher listed? Maybe John Beckwith, Boudreau, or Frank Chance to name a few.

Sometimes, if the second catcher you autodraft is not a catcher as his primary position (like Chance), if you don't get him in Autodraft, HAL will give you a replacement at that player's primary position. For instance, you try to draft Chance as second catcher, but don't get him, then HAL might give you the cheap Yaz or cheaper Ferris Fain, giving you only one catcher on your roster.

My second C was supposed to be Berra at LF, I got Merv Rettenmund instead. Luckily one of the teams in the league had a 3rd catcher and we worked out a trade, which takes the shackles off my opportunity to fully participate in waivers.

I'm not certain, but I think the first pick has to be a catcher to get to a legal roster before any further picks can be made.
Worst case, you list a nickel catcher with your first pick, someone else nabs him before you, and then none of your waivers process.

Good luck.