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

The projects that frankly just suck and are costly but occasionally do happen include a main sewer project (say it collapses), and a roof. 

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.

Built in they early 90's and the roof has been replaced in the last 4 years. 

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

I do not know if it will add value, it may if it is uncommon for houses in the area to be insulated. and for $250, well worth doing, it may even help prevent any pipes from freezing in the future. as far as the electric, i do not find that price too bad, the basement will be easy for them to take care of, the 1st floor, they will have to open up the switch and outlets, tie the new wire to the knob and tube and pull the new wire up using that knob and tube wire and re install the switches and outlets, there is some labor involved and is easier with 2 workers. the lights are going to be the hardest for them to do and they may have to open some walls, i would check with the electrician on that and see if you are going to have the added cost of repair and re painting. a lot of times insurance companies will not cover you if there is knob and tube in the house and it was never disclosed to them, so it would be worth it to you for the insurance protection to have it done. over all though, it seems like a good price.

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).

Meaning if you could get a deal under that it is covered . problem is most dnt know how to get low enough.

floors that are currently completely covered with old wall to wall carpet that we'll rip up once reno is done.