Another factor is that I don't think there is any more than about five years on the roof.

I have been selling my small properties at 11 and 12 cap and they all get new roofs, windows, furnaces, flooring, kitchens and baths as soon as I buy them.

I know with a new baby that sounds unrealistic but just might be the best option in the long run, I'd keep looking for another property you have a roof over your head and can still manage for awhile where your at.  

Landlords,If you want free consultation time to have any of your properties roofs/gutters/siding inspected for damage cause by the elements reach out.

Insulation needs a permit....roof replacement needs a permit...etc.Jurisdictions are different, but if you own the home in an LLC and you are technically not the homeowner (the business is) then you cannot pull a permit yourself unless you are a contractor....this can get a little sticky depending on where you are doing the work.  

We essentially stripped the house down to studs and replaced everything - new HVAC, new electrical, new plumbing, new roof, drywall, carpet, tile, kitchen, bathroom, you name it!

Ideally you would find a company that has everything under one roof.

Closed on a duplex property in Lawrenceville,GA and the roofing is almost the end of life.

I paid 100k for the privilege of leasing the space for 1k/mth adjusted upward and escalated according to the CPI annually.It will be stripped to the frame and rebuilt from the bottom to the top inside and out with a new 12/12 pitched metal roof.

I'm stuck with the roof which has got few tree damages, roof repair costing me 1500 whereas roof replacement costing me 4000.What to decide?