Jon - it seems like (understandably) there are a lot of emotions swirling round in these two posts. You point that out yourself ("I just need to keep getting my crap under control ... it's so easy to wallow in self pity or anger"). It's good that you can vent here. It's also a different voice from the assured, confident tone with which you responded to your W's filing announcement. If that emotional difference is strong for me as a reader; it must very strong for W.
I mention this because I wonder how it affects W's responses to things that happen to you. Those response may not be about challenges but about your responses. After all, she didn't fall in love with you because you were phenomenally successful or wealthy, and your posts about her often indicate that she's kind-hearted but insecure.
So maybe the central issue is not what situations befall you (downturn of markets, theft of bike and so on), but rather how she perceives you to respond to them. Her question may not be, "is this a man who is always successful and who only experiences good luck?" But rather, "is this a man who can handle whatever fate deals him (and can therefore look after me)?".
Perhaps you sense the importance of that distinction when you say "I haven't told W about the Harley yet, wanted to get calmed down and things under control first."
I wonder if you could open that out more by saying what you think the difference in her responses would be if you said:
i. "W! Things are so bad! My bike's been stolen, my luck is terrible! I don't know what to do!"
Or
ii. "W - don't worry as it's now sorted out (i.e. insurance, police), but last week my bike was stolen, but I dealt with it all positively and calmly."
The second situation sounds more like the capable and confident way in which you've dealt with her filing announcement. What do you think? River