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

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

On June 7th, we sent an itemized list of deductions via text; he responded on June 8th, disagreeing and threatening legal action.

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.

Good summary of what your market is looking for but as we all know, each market tends to have its "wish / want" items which differ from market to market.Flow is definitely a selling point but make adjustments come with a cost. 

.- Tenant takes care of most of the fixes and repairs for the property, except for large ticket items that should have been taken care of before the tenant occupied the property.

One quote has the items listed, shows the price of each item as $0 and then has a final total. 

Are these the only items we need to document?

You're investing in RE for long-term wealth, not a few hundred a month that can be wiped out with one CapEx item.

I’ll also amortize large items like roof over 20 yrs, and then add $100/mo/unit for general repairs.