Clearly you're versed in numbers and assessing alternatives so surely you'll identify the optimal path!

I am in Cape May, and we are allowed to do as we wish down here, although the season is a 7-day minimum.You actually stand to do well and have less expenses and wear and tear from multiple turnovers, but those 30-day tenants don't grow on trees, so you are going to want to market hard.Please tell me you aren't relying on AirBnB in NJ - Tenants pay 20-30% more here and you get none of that overage - booking direct saves them that service charge and taxes, so you could actually up your rent and collect more yourself and they'd save $$.

This thesis statement was driven by the collective understanding that there are significant rental inventory supply issues in most markets in the country.

With no experience and little knowledge in real estate, is there a strategy I should consider just to get the ball rolling and collect knowledge?

Hard to say from the short post here which is optimal.  

BP, I've been on a long search for technology and applications that allow me to automate parts of the tenant journey (leads, apt tours, screening, rent collection...).

Building relationships and rapport during property tours can also result in unforeseen rewards, such as sellers leaving equity in the transaction because of the trust and connection formed.Remember, every property tour is an opportunity to collect information that is not available on paper.

Generally speaking an investor collects rental income and signs a lease with a tenant whereas a flipper or developer shows "inventory held for sale" on their books and gets all of their economics derived from a SALE.

The biggest issue for them is that quite often Class D neighborhoods attract Class D investors, Low life investors who think that they can buy for pennies on the dollar, invest peanuts into the rehab and then collect free income from the government for years to come.  

Which is the core of my question in the start, does it matter for the lender if I pay directly using the LLC's bank account that collects the rent or I take that money out from the LLC to my own they pay as I do now.