The right property owner you are looking for is someone who are looking for long term stable income, don't mind take a little discount and maybe waive the first month rent if you can somehow convince them.

Property manager had pest control come and they mentioned “partial exclusion” on an invoice, and calling the pest company I found records that they sealed up those drains.

We use it exclusively for all of our REI Clients.

I would go with a hail resistant 30 shingle then you get a discount from the insurance company .

Problem with many of them I see this far north is November thru March they kinda sit or you have to discount the daily rate so much that you only might break even.

Particularly power related tools since those are usually discounted for Black Friday. 

For one, the rental income tends to be lower than with short-term stays due to the necessary discounts, yet we still face most of the usual costs, aside from savings on cleaning and supplies.

Assuming you have a one year contract with your realtor:Apart from the usual buyer representation commission, do you have any exclusive clause with your realtor?

The good news is that if since it is being used for investment use, you could also qualify for a 1031 exchange and take advantage of the 121 exclusion.

Ive certainly purchased properties at serious discounts to the listing price....but it wasnt just random shotgunning of the offers.What I usually start with when trying to see if a lowball offer is appropriate is having a conversation with the listing agent first.