Their ability to recover their money should you default is much lower in this position.

He can spend the next few years-ish getting a finance degree through an online school while working part time, but he just got offered a full time position helping with sales for a local wholesale real estate company. 

But if your goal is to cashflow positive from the Day 1, you may find it very challenging due to current day interest rates, high cost of construction and the fact you won't have the efficiencies of a seasoned developer building at scale.

Possible (but I doubt easy) if seller takes a 2nd / subordinate position to the bank or is secured by other property you own.

It can be a positive for short term rentals (if in a good area) to be near the airport.

I just re-read and realized you're talking about getting loans for lien position 2, is that correct?

Based on my calculations, even with a low down payment, I can achieve positive cash flow (with aggressive enough house hacking).

Hi KyleThe way most real estate for sale is priced these days there’s little to no cash flow after debt service with 25% down - borrowing a down payment would put the investor in a negative monthly position. 

How do others manage to create positive cash flow from MF properties with debt?

Your cash flow is positive on paper, but how will that look in reality?