IT - Marketing - Financial - I’m just trying to get some deeper insights into a business I want to start that focuses on making services cheaper to small and mid size businesses with solid customer service.

I'll dig deeper to find more info. 

Once you dive in, it should become more apparant with time what "niche" will work best for you based on your personality, your abilities, and your finances. 

While Redfin/Zillow, etc. have become more robust, they have limited information when digging deeper relative to the actual MLS.

We are looking to dive into a new market.

Just dig a little deeper on them and you'll normally find these problems

I'm looking to get into real estate investing (buy and hold in particular) and am trying to learn as much as I can before I dive in.

Sounds like you have everything you need to be super successful at real estate investing, now you just need to do a deep dive in studying REI.I’d highly recommend reading and listening to entirely too much content.But, if I were you...I’d use the money for down payments rather than using it all to buy one property.The reason for that is the power of leverage.

I'm looking to get into real estate investing (buy and hold in particular) and am trying to learn as much as I can before I dive in.

I have few in my list who I am reaching out to dig deeper on the areas that you mention and also to gain more knowledge.Thanks @Josh Bakhshi