Even then my stock performance was dismal compared to RE even considering investing a lot more in the market.

The insurance company was pretty reasonable to work things out with even though it did not start out that way, and they did have my blood pressure up considerably!

The cost of eviction is really high in NYS, the cost of mismanaging an asset is even higher. 

Hard to answer what to look for without even knowing what you're trying to insure - there are a lot of types of rental properties.Landlord and homeowners insurance is not the same though the types of coverage are similar.

After acquisition, we had gone on to discover that this property was even more ideally situated than we had previously realized.

From a lender's perspective, that type of loan would be so incredibly complex that it would have to really be worth the lender's while to even consider doing it.

This criteria is for 1-4 and 5-8 unit programs.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 = 1.23DSCR lenders generally let you vest either individually or as an LLC.

Getting into a property that has negative cash flow can seriously hurt, even if you've thought out a magnificent plan for it.

Even after I complete the 5 years of the 2/5 rule?

You wouldn't pay more for a home with a really strong tenant b/c even the strongest tenant typically has <12 months left on the lease.Take a look at the cap rates.