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.) 

No holding cost, no tenants, no insurance, no leaking toilets.

Your first is already risky enough since you lack experience, combine that with 100% funding and the risk is through the roof.

About a month ago I had a contractor replace a roof that got damaged from a storm but when they had the shingles off another storm blew through overnight and blew the tarp off and a lot of water got in the house.

HVAC, Plumbing, Sewer, Roof leaks, etc. 

Hey @Devin Bost, I would highly recommend a few things to help with this. 1) Have systems and processes lined out for any emergency you can think of.2) A spreadsheet of subcontractors/ vendors that could handle the situation that arises (plumbing leak, electric out somewhere, etc.)3) Your cleaning team and handy person should be utilized for some things.4) Something like Breezeway can give you 24/7 support around your property with a dedicated phone number line.

If the separating wall is a load bearing fire wall, it would have 2 sets of framing material on either side, essentially you have 2 completly independent houses joined by the roof, you can go in the attic and see if you see sheetrock going to the ridge of the roof. 

This helps me with pricing, and I try to keep those prices current so I know what to expect when putting on a new roof, or replacing windows.  

Got it.What we include in the process as well, is "how best to protect yourself from the "due on sale", what happens if the renter stops paying, what if the seller won't vacate, how to get a title report, why to not use a real estate agent, how does this affect my taxes, what makes for a good deal, what exit strategy to use, how do I hold title, what happens when the seller comes back later and demands to be taken off of the loan, how do I hold insurance, what happens when a roof or waterheater need to be repaired or replaced, and on and on.