There is a ton of fix and flip going on in Brooklyn and I am trying to work my confidence towards that after my first project at a lower price point around 300K somewhere (CT seems like my only option). 

Seems like you're in a good spot with lots of options.

Your criteria seem a bit strict for Section 8 applicants.

It seems to me that they all whether paid of free, will all have the same exact amount of houses because all the transactions are all public and so they seem to compete with each other based on the quality of the data of the houses, how up to date it is, and the user experience in configuring the how the layout is.

Private equity firms seem to favor larger operations with scalable systems, while smaller mom-and-pop firms are often acquired by local players or regional operators looking to expand their footprint.If you’re looking for actionable intel, reaching out to brokers specializing in the sale of PM firms could provide useful leads.

They seem to have a good team but this is something not thought out it seems , in their support I do have DSTs which have had the same issue and have not been making payments. 

While it may seem daunting at first, beginning with a clean slate allows you to establish clear expectations and build a strong landlord-tenant relationship from the outset.

How do you handle scaling once you get your first property – is it as daunting as it seems, or does it get easier?

Even when talking with some real estate professionals who would seem to have an incentive to help me with renting out my property, I have been met with serious warnings (they pretty much say don't do it).

STR seems like more work.