That being said, if you're williing to persevere and the insulation has never gotten wet (roof leaks), it will still perform fine.  

Roof looks ok and siding looks ok, but inside could be a total gut.

Look at when a big repair will be needed like ac or roof. 

Hello,I need the following work done to my house, which is located Intown, to get it rent ready:- New roof installed- Tree cut down, basic landscaping and exterior fence repaired or replaced- Rent ready finishes - new kitchen cabinets, new doors, fresh paint, refinished hardwood floorsThis might be too small for a GC that is used to larger projects, but the roof is something that I would assume I should not be leaving to most handymen.

They may never reach it or they may go over 50% take your pick.What will it cost to replace your roof in 25 years or what will your rent levels be at.

The roof is old but holding up well.

@Akilah Smallwood  I passed the house this morning, it's still for sale and the roof is covered in pine straw.

@Robert P. thank you for that info about how it is done in Mass  i will look into that info for NY@Matthew Paul i purchased the property for cash, so as far as not having income i will not have a mortgage to pay for, the reason money is tight right now is because i had to pay school taxes right after closing, and then spent $17000 on a roof the first month. 

Once it started raining some leaks became apparent.

When you're a landlord you need to remember you are providing a roof for someone's head.