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The cap is just a message that you can't do more towards any milestones at that day. You'll get that whether you're progressing on something or not. Maybe your Sims just hasn't progress a certain livestyle enough to be considered in progress. It takes a while playing the same style for the to advance.
There could be a problem that the progress reset when switching families but I haven't seen any reports to that degree.
I would just play on for awhile and see if anything comes up.
Earlier while playing I browsed through my MCCC mod and found where I could "add" a lifestyle to a sim. So I picked one, and it now shows up in the Simology panel as "in process". I think I was a little confused by the interface. What I was seeing was an entire panel of "locked" lifestyles. Now, in this sim's panel, it only shows the one lifestyle I added (people person) plus empty spaces for 2 more. So maybe for now I'll just manually add lifestyles for my sims and see where the game takes it from there. Thanks for your reply!
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