Last year on one cabin I had to replace the roof, hvac, & tile shower which came out to $22k.  

Has a unique garage that is open air, but  roofed and on the same slab as the  rest of the house. 

I just closed last week on a duplex, new roof, windows, siding, furnaces, HW tanks, all cosmetic for ready,.....70k, Rented for 1800.

Savannah all I have is one of my houses has a damaged roof, that's it and feel fortunate.

If not, I suggest waiting until you do.If you use up all of your equity on your current home, rent it, and then need a new roof or boiler, your attempt at your first door will go sour.

Now, you have an appreciated first rental that’s hopefully generating cash flow, and a multi unit that provides a roof over your head and 1-3 units paying down your mortgage while all units continue to appreciate.

I tried to estimate what a GC might cost in my calculations, but I have an uncle who does roofing and cousins with window installation and landscaping businesses, so I believe I can save some significant costs through their help and guidance. 

Multiple times projects took so long to get started or to get an appropriate bid, I ended up having to handle it myself (ie. roof replacement, unit turns, etc.) 

Your HOA will likely keep increasing and because of the excessive heat, roofs get replaced more than in other areas and if the HOA is not super liquid, that will come back to you in the form of an assessment.

We have also found our that the sellers lied on their disclosure of what they knew about the hail damage to roof.