However, a lot of concerns can be mitigated with looking at their past rental behavior in a lot of different settings.

That "pipe" is known as a Line Set. 

If you want help with setting up a profile, crafting an outreach message, or anything else, just let me know!

I would like to use this life adjustment as a catalyst for my entrance into real-estate. 

One of the turn key companies that I found through bigger pockets doesn't have properties available in the areas that this new company I working with could potentially set me up for.

It’s a little more work to set up, but if you get a solid property manager, it’s not as scary as it sounds.If I were you, I’d keep digging into the Capitol region, NJ, and CT—compare the numbers, and maybe even start building connections with agents or wholesalers in those areas.

With $330/m in cash flow, unless you have sufficient reserves set aside those funds should remain as liquid as possible in the event of repairs or cap ex.

I offer an online payment portal to submit rent payments via ACH or CC - they "couldn't figure out how to use it" so I set us up to accept Zelle payments.

I’m not convinced it makes a real difference unless a person has a unique setting.

Those rules are set by Fannie/Freddie NOT your lender, or any other lender in fact.