As Jay mentioned they must be NMLS licensed if owner occupant of in several states even commercial needs licensing.The NMLS is like the database, each state has a division of banking that oversees lending requirements then you also on the federal level have CFPB as well as consumer protection laws.I want to add that I believe yesterday the CFPB is undergoing changes, but if it goes away that does not mean that many of the laws in place especially consumer protection laws would go away. 

IIRC, RW even charges hourly rate fees if a property consumes too much time. 

Use your evenings and weekends for follow-ups and networking.Sending text messages could fit into your schedule too!

From my understanding, no one is employed, they are somehow current with the rent, but they are definitely not someone I would offer a new lease...not even at market rate.  

Meaning, is there a way, maybe even after my 2nd purchase, to only use my properties to continue to scale?  

If you find something that works well as a short-term rental, but doesn't work well for you as a home, you'll have money but be dissatisfied when you live there.You don't even need it to produce a profit.

Given these numbers and his research, he believes it may either cash flow slightly or at least break even, which has made it a bit more difficult to find an end buyer. 

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

Since Landlords are going to be monitored even more now with the price gouging issues surrounding the fires in LA, I would be extra cautious.

Our professional incentives are fundamentally different, which makes a meaningful discussion about financial strategy even more critical.I also have to ask: Are you ever curious about financial strategies other than insurance?