Replace roof or not?

[Junior Francica]

Hey guys appreciate the insight and help. 

Got into my first flip and just started the rehab work. The roof of the home was redone about 5 years ago so no issues with the roof. In the original plans for the fix, the roof wasn't calculated but have already been able to save some cost in other areas and now the contractor asking if we want to have the roof redone as siding and gutters get redone because its asphalt shingles (believe that what type), essentially just really ugly. The Contractor is a personal friend and already said they would do it at cost if we wanted to add it on for 5-6k total. 

My biz partner also considering it for aesthetics and resale.  

Have you guys ever redone the outside of a home and not the roof and regretted it and vice versa, ever redone the outside AND the roof to look better and been glad you did? any insight would help.