If not, then the 75% rule can apply but only to offset a maximum the housing expense for the subject property with no additional overage to help your debt to income ratio. 

My biggest hurdle with section 8 is finding a turnkey property that doesn't require a ton of renovations.

No one wants an eviction on their record.

No matter what you don’t ultimately want to pay for a tenants AC or Heat because they have no incentive to conserve it.

I wasn't picky, just particular...no, not particular…thoughtful.

I have no personal experience with them but I am skeptical.

I assume all your policies are giving you a discount for no claims.

The biggest lesson I learn, is if you want to do it right; read and follow David Greene's book 'Long Distance Real Estate Investing'Good Luck!

(Question 1)My friends expressed concerns about Steve potential retaliation, maybe in ways that I might not be able to directly identify him for (e.g. causing damage to appliances in the common area and I would have no way of knowing who did it.)

No reason to get ahead of yourself early on.