whats his premium for awaiting payment, etc.Whats the best way to attack something like this?

It takes around 2-3 years for a website to rank organically and produce deals.As most deals today can be listed an sold as is to regular non investor buyers for a premium.

One thing I noticed is that the 4 BR's were selling at a premium over the 3 BR's. 

However, you saved $24,000 by paying a lower premium for the last five years so you actually have $34,000 towards the roof replacement. 

The only thing I'll note, because I work in the insurance industry, is some companies give a discount if you pay the premium in full (which the escrow does). 

I saw that you said the property manager has a lot of experience with turning units to get them reno’d so maybe the additional 6 months to a year of rental premiums could be your hedge on that $50k in repairs that needs to be completed, as long as it makes sense for you guys.

As an example, generally speaking right now Storage is a "Hot" market where sellers are getting a premium for properties in many markets. 

So I know I’m paying a premium to have this done. 

Whitepages Premium is great.

They are enrolled in our master policy and charged for the premium monthly unless they provide proof of insurance.