The rent I should be able to receive should cover all costs, including insurance, taxes and hoa with excess.

One had lots of hail damage and the other one was 30 years old and had excessive granular loss (you could barely see any rock left on the shingles).

*That may be excessive to some people, but I worked in the healthcare field long enough to know that even 500,000 can be gone in no time with just one severe injury. 

As Josh noted, some people prefer one over the other, and that's why I think your intent to do both is so wonderful - because you are willing to cater to that which the audience prefers, without excessive clutter.

I'm an underwriter at a commercial bank and you are going to want to look for a community bank for this type of loan.Be prepared to pay a little higher interest-rate, but as I like to say don't lose sight of the forest for the tree's.The biggest thing you can do is to create a spreadsheet showing your cash-flow and respective debt-service and how you can easily pay ALL of your debts with excess free cash flow.

If the insured does not have sufficient personal liability insurance in excess of $300k and a $1 million dollar plus umbrella policy or if the insured lives in the property a more robust DP policy will be in order along with the umbrella and flood policies.Individual HO-4 policies will be needed for each tenant but that is the responsibility of your tenants. 

Though I may add that in some jurisdictions (here being one of them) you are not allowed to request/collect a security deposit in excess of one months rent.

I have seen limits on repairs in contracts, so anything in excess of $250 has to be approved and multiple quote provided.

Two months rent and get ready costs seems excessive.

Not to be a deal spoiler, but if the property goes to tax sale the owner of record will get all the excess proceeds (assuming the mortgage is really paid off and there are not other liens).