1DAD your post has got me thinking.
I don't intend on ever having to date again and have never done OLD, I met my DP in the pub when least expecting it and we get married next year. However, to put your theory to the test hypothetically speaking, had we met on OLD and he was of the same school of thought as your OP, we probably wouldn't be where we are now.
We had both not long come out of a LTR, I had a dead end job as I had moved counties to go back home when I split up with my ex and I was on the verge of bankruptcy amongst other things.
I laid it all out on the table on our first date (with the exception of the financial matters) and he still asked me for a second date (and he didn't even get a kiss!), I eventually told him my financial woes a few weeks later, he again couldn't care less. I actually never ended up declaring bankruptcy but still had/have (quite a) bit of debt from my previous relationship.
So, from my perspective, I also wonder whether circumstances contribute to the overall feeling about someone's baggage, or whether regardless of how a person ended where they are at that point of meeting, you would write them off anyway?
As for me, my finances were in such a mess as I was working 2 jobs (a pretty decent office job and a normal weekend job) to pay a mortgage and all bills while my ex sat on his arse all day telling me he was looking for a job and was too good to claim JSA. He was in fact watching porn all day.
I was only in my dead end job for the first few weeks of our relationship and I now have a pretty decent career I am proud of, as well as more qualifications and I'm only really just starting on my chosen career path.
5 years later and we have travelled the world, have a lovely home, a beautiful daughter and, as I said earlier, we are getting married next year.
My DP earns substantially more then I do, he had a house deposit sitting in the bank waiting for him when I met him and didn't have any baggage or responsibilities, but my liabilities didn't put him off me when we met and we are now happier than we have ever been.
It does make me feel sad that had he looked down on me for being in the position I was, that neither of us would have experienced the things we have with each other or be in the position we are today.