I read the permitting process and it seems somewhat strict.

To me, having one mortgage payment for 2 - 4 houses (basically) always seemed interesting and like something that would give me more bang for my buck. 

That seems low with the 5 units and storage you mentioned unless they are 1 bed units. 

To leverage the equity for financing my next deal, a second mortgage seems like a more cost-effective option.

Now as for what happens if a person who just lost a million+ dollar home just bizarrely says "nah, forget it, being a bum in a tent on the beach seems so much better".... well if ya knew the basics of Real Estate you'd know there is policy in place literally everywhere in the US for exactly that.

I've talked to two local agents about possible price points to list at, but it almost seems like they are pulling numbers out of a hat.

It may seem easy to jack up rent but there is something to be said about good, on-time paying tenants.As an accountant, I always rely on the numbers.

Lots of older houses but there seem to be several that have the potential for cash flow and while not exactly modern on the outside, have been renovated inside. 

That seems a little odd, I still send out text messages and I dont have a website.

It seems like the tenant is being respectful, following the rules, and is not being a problem so I think that is what you would tell any other tenants who ask, as long as you have seen the card.