Earlier, I was doing the quest where Cass tells you to go to the Crimson Caravan company and get work. I get there and find the boss, that Mclafferty or whatever her name is, and I go through all dialogue options. Then I get the objective to try to chip on around the town, and the objective marker is still pointing to Mclafferty and when I go to talk to her all I get are the options to talk about the history of the place, etc and then the goodbye option. Nothing about doing any work. Is there some sort of hidde prerequisite to this quest, or is it glitched for me?

you have to do a few quests she gives you before she eventually gives you a quest to get cass to sell her caravan to her, and then you can have her as a follower

There hasn't been a major glitch reported with this quest.

I'm not sure what you mean by "Chip around the town"

McLafferty has three objectives (And one optional one.). You can take them one at a time or all at once. This is the You Can Depend on Me quest. http://fallout.wikia.com/wiki/You_Can_Depend_on_Me

You may have started the Heartaches By The Number quest. This one intersects with the other one. You can do both at once but the order is tricky and it's easy to get mixed up. The key is to ask McLafferty for work and do those three jobs. Here is the lowdown on http://fallout.wikia.com/wiki/Heartache_by_the_Number

Remember: The Wiki is your friend.