Given the roof is likely a 25+ year life, and you are likely on a 5 yr term, you should not be paying for all 25yrs of that roof.I would also want to know age of RTU, and have limits on your costs.  

Rob,Welcome to investing and at your age you will have much time to do well.

But one of the things I learned at a very young age, was in business, always deal with professionals who have the most experience where experience is needed.

Also, the average age of these owners is 60 years old with on average 15 years of ownership... 

There is a distinction that NYC makes when it comes to "habitable" vs.

Then they add or subtract for location, age, size, etc. 

Those you could see yourself when you looked at the house . put on the 5 year list .The deck , without seeing pictures is hard to tell , could be age , could be poor design , may or may not be expensive All in all that report wouldnt scare me at all ,  Its an older house , it will be constant maintenance .

You're paying for a brand new build (with high build prices) but people will associate the age/condition with the existing old/leaky structure.

House that's been owned for ages, same owner or tenant for years.

This post has aged well. 5 years ago it was still easy to buy in Milwaukee, even in great areas.