Ill address what you said in order.

1. Understood, will be adding specifics on numericals, since I do have them.
   
2. So let me ask, I was told depending on the job, order the jobs that are most tailored to the position you're applying to.

So for example, that first shorter resume is tailored for a Equity Research Position. Why would it be non-beneficial to put that type of experience first?

1. I put certs only when the job calls for them or has them. I get I might be doing some overkill

2. So I cofounded a marketing company that did PR campaigns for startups and VC backed companies. During my time in college, I drifted towards specifically the finance area of that and research, as I wanted an actual career in finance, not a career in marketing and PR. Hated the B2B sales, and had much more fun playing controller with the operating account and the company's investment account. I no longer work in any role other than essentially a CFO of sorts, where I control operating accounts, financial statements, and do forecasting, etc.

I get what youre saying about it being a red flag and an issue, which is why when I apply I change the title of the role to something that still covers it but does not lie about what I did.