I will be eventually moving into this property as my primary for a year to maximize the house hack.Just be sure to read the fine print on use of proceeds as I’m sure each lender is different.

If it looks like the roof is fine now, bu will need replacing within the next 5 years...replace it now. 

It can be illegal if you are not following the telemarketing laws however and their are stiff fines if you don't.

@Shawn Skaggs I think the way that it is structured is fine.

Fine rate but that is a lot of points on an investment property.  

Your strategy sounds fine.

The long term rentals are doing fine as of now.

I think tenants today (especially younger ones) are fine without doorbells. visitors simply send a text when they arrive. nobody wants unsolicited doorbell ringers anyway.

You have to have a contractor you can trust, a property inspector that can go over the property with a fine tooth comb if you're not familiar with all of the aspects of buying a used home, a lender/broker that has the products and a property manager if you're not experienced or if you have a real job. 

Even if you don't have reserves, you should be fine since it will appraiser well.