Apologies not (ever) required. The forum is very rich, and the search tool is somewhat limited.
Like me, you have a deep background in IT (I am fast approaching my 40th anniversary, which can make UML a greater challenge than it might otherwise be.
Tricks include forcing yourself to think in an object based way (I am purposely avoiding the phrase "object oriented" since it is overloaded here). Don't try to do the same things in a better way; try to do other things that will get you to where you should be going (i.e. things that are just as good as before, but put you on a better path to a better end point).
For example, there is a clear evolution from variable oriented programming, through abstract data types (you'll remember your old books from Aho et al), to object orientation. We all know that. What is so obvious that we often miss it, is that in order to be effective, each of these paradigms force you to think and work in a different fashion. Each asks you to un-learn what you knew before. That is, each approach may be invoked to solve the same problem, but the solutions themselves will be very different.
Now, taking that into consideration, reflect back on what you've seen, and consider not so much what you could have 'done' differently but on what you could have 'thought' differently, given that the end product (perhaps versus the goal) is different in each case.
Not much help in a direct sense I know, but I'm trying to compress quite a bit of tailchasing I did when I went through this.
David