Going to paint the front of our rowhome's bay window and roof cornice details with 2 colors.8.

Got my first roofing issue with my first rental and need some good references.  

Won't be able to do roof 25 year life span, appliances and hot water heater 12 year life span, hvac 20 year life span, bath and kitchen remodel 20 year life span, etc.

So far I have had the boys strip a roof (used contractor to put on the roof) - resulted in boys in landfill jail for not having the cash (I did not know no credit cards) - boys claim there were 7 layers, take down 2 large trees, add 3 sister boards to a garage rafter, build 2 fence segments including an 8’ high fence, add dumpster stops to concrete to prevent fence damage, add privacy screen to a chain link fence (took surprisingly long - hog rings really do not work well), remove and rebuild a privacy partition on to a wall, rehang a gate with better hinges, weed an abandoned yard (unit caught fire in oct and due to Corona work has stopped - slightly wet winter and weeds were 4’ tall), plant a new citrus tree.  

Ive been told by several that maybe the roof is an issue which is the biggest expense.

You save a lot more to check for SER and determine there are duct leaks or maintenance issues with both furnace and compressor. 

My capex budget includes roofs 25 year life span, floors 10 year life span, appliances and hot water heater 12 year life span, hvac 20 year life span, bath and kitchen remodel 20 year life span, etc.

Family member (the owner of the adjacent condo with shared roof/wall to the condo for sale) wants to split this deal 50/50 and suggested wholesaling. 

Have you ever had an older roof that you were told needed to be outright replaced? 

The same tenant owned a roofing company and we made a agreement on the roof for two free months of rent in order for him to do the roof.