You've given me some solid pointers/items to take into consideration for future deal analysis, so thank you for that.

You missed an important item: Depending on how a person does #1 or #2, it could get them: A fast-pass to the "Principles Office" for "bullying" and now there sitting in "detention".... 

I know building a reliable local network will be key, so I'm hoping to connect with experienced real estate team in the area.The military presence in Jacksonville catches my eye, and I'm particularly interested in properties that might appeal to military personnel and the associated contractors.

The following are the key items I would recommend investors pay attention to:A. 

But, there are certainly several items that would give me pause.  

Tailor these amounts to the significance of the task; for example:Roofer: $1,000/day (critical to weatherproof the site).Painter or garage door installer: $100–$200/day.Contract Value & Payment Terms:Agreed payment amount (lump sum or itemized costs).Breakdown of payment terms:Deposits.Progress draws.Retainage (if applicable).Scope of Work:Be as detailed as possible.

turnkey section 8 is not going to be like buying a brand new home there will always be differed items or stuff that does not work etc.. age of homes makes this impossible. then you add section 8 tenants and  there you go

It can potentially be deductible as an ordinary or rental expense, an itemized deduction or simply non-deductible. 

Pack their items, change front door locks and give new locks to other tenants.

Additionally, they should help with coordinating your home inspection and if needed, getting GCs to walk and get you an itemized bid as well!