I haven't filed a claim all these years but insurance is for the what-if and to be used for the high-ticker items, but chances of damages exceeding the 5% is low.  

Giving them a laundry list of items will typically just overwhelm them and create more confusion instead of giving them a smaller step process to get more confidence to get the ball rolling and then they can get into the weeds on their state when they get the contractors out there, have local bids come in, and dial in their plan. 

Look at insurance and tax costs, those two items are the biggest killer of cash flow.

At the end i will add a list of items why adding a single ADU in single family zoned areas may not be the best RE option.The most common value add is via a rehab.  

A savings to put deposits and another account for everything elseyou don't need separate bank accounts as accounting software will classify all of those items.

Slippery slope if you ask me, and dangerous if one wants to avoid courtrooms.

I think negotiations on knocking the price down on inspection items on value add will be huge especially if its a flip like you mentioned.

When it comes to assessing maintenance costs, one of the best approaches is to request itemized breakdowns for larger repairs.

Also, what others have said, the personal touches on what is in your place (e.g. providing all the essentials instead of having people buy TP, coffee, shampoo, etc.) and the quality of those items (no tattered towels, stained sheets, etc.).  

In my area (near the beach) its mostly families and they want cabanas, baby items, chairs, coolers etc that we do not provide but I have a local vendor that delivers and picks up these items and charges a few dollars per day for each item, and give me a 20% referral.