One of the accounts covers almost all of my bills which are all automatically deducted. 

Try to include pictures and other evidence to support your claim.

Like anything there, will depend on what your other options are on those risks....Other risks include more of the macro picture stuff, which mostly has an effect on the equity picture of your properties. 

Every city has its own mix of 'good area' and 'bad area' thing going on to some extent, but the bigger picture needs to be solid firstly.Beyond that, I think you're touching on numerous different things here but my mind would be on getting actual numbers/data. 

And this time I hope I can do a better job because I am sure I got my back covered with pros at BIGGER POCKETS and hopefully local Reia which I am about to join soon.

How much insurance coverage do you have and does your policy even cover a dog large enough to jump a six foot fence?

First, our winters here in Boston can be rough - and tenants can be very sensitive to issues due to lack of insulation (cold spots and drafts) Second - big picture you may not have this property forever and will need to insulate before selling because that will impact how a potential buyer will value the home.

On the one hand, at $325/night, you only need 8-9 nights per month to cover your mortgage, utilities, and cleaning. 

I purchased a two family house in NY almost two years ago, but to purchase that home I took a pension loans and a personal loans to cover some of the closing cost ( 70k).

Really depends on your loan picture.