As for the 5 year annualized, that’s a number we get from the bigger pockets rental analyzer.

I'm analyzing properties in my expensive market which has a dire need for affordable housing.

I am hoping to learn more about how investors analyze their deals and make decisions, as well as looking to better understand general real estate investing.

Analyze the property and determine what price you are willing to pay, then offer that amount.

In this order I would analyze the rate of return. 

Look, we’d all like to search the internet, find a deal for sale, analyze the property as having a great cash flow at current interest rates, with lots of upside potential in a gentrifying market.  

I'm looking at investing in several out-of-state markets (potential BRRRR strategy in mind), I have a list of qualifiers that I'm sussing out to determine viable markets but would love to know: what data helps in dete...

Without a firm base and working familiarity with these three areas the investor will not have the knowledge to analyze, negotiate and close advantageous real estate transactions. 2- Experience - the first few deals are likely to be smaller, harder, with more “surprises” and not as profitable as the investor imagined.

How about just 1 who "analyzed/ researched" themself into success........ 

But perhaps you would be better served helping a local experienced investor find deals and ask them to show you exactly how they analyze deals, what's good vs bad, how do they finance (debt vs equity) etc etc and understand their business model that has a proven track record by providing value to them.