(I'll be walking through it early this week and will learn about the state of the roof and any updates to mechanicals.)The property is a 2-story, 3 bed/2 bath, 1650 sq ft SFR built in 1899 in an area dubbed the "Historic West-Side" of my hometown.  

The building looked fine to me and the roof is 7 years old, but just the fact that they are witholding the financial information is making me think there is something else going on here. 

You won't need a roof for 30 years, you probably have 6 years of life in the HVAC system, there likely won't be huge plumbing issues, etc.

Up on the Roof, by a roofing expert.

The next deal I made an offer and after the inspection there was a roof issue (15-17K).  

You might also see 10% cap rates on older properties/areas where maintenance is a little underestimate and you're 2 years from needing a new roof.  

Sitting on the sidelines with a pile of money is nerve racking, but needing the money and not having it can be much worse. 

The roof looks very old, but no signs of damage.

Drywall is in, but it needs flooring throughout, kitchen cabinets/counters/etc, bathroom showers/vanities, new roof, and possibly new windows/sliders throughout.Any recommendations?

@Brandon Leong my experience when getting insurance is my insurance broker tells me what the coverage is based on several factors that I give to get a quote (I've gotten quotes for SFR and quads):1-how far from fire hydrant and fire station (she figures this out for herself since I give her the address)2-roof age and here in Florida, wind mitigation3-age of property4-is it in a flood zone5-she does a minimum mandatory coverage amount and then I tell her how much more in $$$ I want covered. this is based on how much will it cost to rebuild.6-the rental loss is included so I don't need to ask about that - at least for me it is, not sure if others have to ask for it to be included.7-what type of electrical and plumbing are in the house if it's an older home.Perhaps talk to a insurance broker and tell them what you have and ask them for a quote.