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

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.

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.

Not sure it’s in the budget to add any more gold fixtures or a new island to the kitchen, but I may replace the towel rack in the bathroom. 

HVAC duct work insulation is also deteriorated.No vapor barriers installed eitherSome fungi/mold growth notedPlumbingMultiple small leaks under sinks and from bathtub and toilets.House has Polybutylene plastic plumbing which is dangerousMain shut off valve is damagedElecticalSome small exposed wiring and bad splicing.Whole house has no GFCI's or grounding outletsInteriorMoisture spots on ceilingExteriorLose Vinyl SidingDoor Jams and Window trim have moisture damageDriveway need replacementRoofingMinor leaks noted in atticRecommended to replace roof covering, but not whole roofSome fungi growth noted in roofSo some of the question I am trying to tackle with this work is:How much should I budget for the main issues listed? 

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. 

In the spirit of "I've finally resigned myself to the fact that AppFolio has me by the balls and I'm trying to do everything that we can directly in AppFolio" I'm embarking on a journey to set up inventory management in our shop storage racks and managed in AppFolio.

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.

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.)