The same goes for an excessive number of small holes, like a single wall with 40 nail holes.

You can compromise without loosing good paying tenants if they pay on time. 

I regularly get sent underwriting on value adds in excess of 20%.I do not do work intensive value adds to flip so my acquisitions have slowed significantlygood luck

I don't know what they are but unless there's something in the city that requires that kind of notice, it sounds excessive to me.

He is a contractor by trade and I am the sales and numbers guy to loosely define us.

When a tenant moves out, transfer the deposit back to Checking so it's ready to apply towards expenses or refund the Tenant.If you end up with excess funds in the Checking account, I recommend you transfer it to a third account designated explicitly for future investments.

A possible solution could be to hire a handyman to cut out the section of drywall that has been water damaged and use a moisture meter to see if there is excessive moisture in the wood and other parts of the drywall. 

It might be worth a follow-up closer to the move-out date to confirm their plans, but avoid excessive contact to prevent escalation.

Some packages genuinely improve property performance, while others might feel excessive.

I find that putting a utility cap in the lease agreement they sign and calling their attention to it really helps make them more aware that they'll have to pay for excess usage so, fortunately, I haven't had to actually bill anyone yet, but the language is there if I needed to.