Try to be positive and understanding since there were lots of factors that led to delays.

They got Jared a policy that ran around $4,100 a year, which wasn’t exactly pocket change, but it felt like a workable number once he factored in the premium he could charge per night.

Use the following as a "Factor" for discussion and not as exact. 

Market fundamentals and economic factors seem strong and promising.

Once again, the loss of the compounding factor by concentrating on my personal home rather than an investment was significant. 

That’s before factoring in utilities or each personal situation.

The differing factor, IMO, is whether you're working with an HML/PML or a traditional bank/credit union.

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).

I would factor more vacancy as you might get more turnover compared to other suburbs. 

When analyzing your offer, make sure to factor in operating expenses, rehab costs, and vacancy rates.