One of these are requiring me to replace the roofs on 2 outbuildings on the property I am purchasing within 30 days of binding coverage and want a signed contract with a roofing company prior to coverage.

For example, who pays for fixing the front patio roof if the roof is a continuous roof for 6 adjoining row houses? 

Let's assume that in 15 years you will have to replace the following: house roof, refrigerator, a window that broke, and to retile the bathroom walls.

NOW, as a buyer, I can understand how helpful it is for me to have the TDS before I pay to have any inspections completed, because anything on the TDS related, for example, to a past roof leak could be looked at during roof inspection, or related to a past fungal/dry rot issue could be looked at by pest inspection to ensure the past repairs held through time.

Entire roof had to be replaced including roof on detached garage.  

The roof and A/C were just replaced, I would have have to put in a couple appliances but nothing major.

.- Exterior paint, interior paint - HVAC and water heater appear new, roof appears new- Interior has some water stain marks, replace drywall patches- Replace kitchen with modern cabinets, granite, appliances- Oak floors downstairs hopefully can be refinished- Replace carpet upstairs with composite flooring or nice carpet - stairs are carpeted!

Or suddenly it turns out the roof wasn't in as good of condition as it seems and starts leaking badly and needs large repairs or replacement and you only have $2,000?

And, like Capital Reserves, a part gets squirreled away so that in 15 years you can put in a new roof..Again, if it's done correctly.

You could learn marketable skills that can put a roof over your head and food on your table.