I am in Pittsburgh so I dont know if the process is different in your area but sometimes you cant sell the property with good title for up to 1 year so your holding costs can be excessive.

I agree that charging each landlord $250 to maintain this list is excessive.

To address that, we underwrite our deals to a 10 year hold, with 10 year financing and excess cash reserves.

An umbrella policy provides excess liability coverage above and beyond your underlying policies for those worst case scenarios.

I set aside a large portion of my excess income that I use for investing.

I charge each unit an additional $25 per month and just eat excess water charges if any.  

You could charge them 1/5 * $1000 = $200.If damages exceed the deposit, and you're confident they will stand up, you can send them a bill for the excess. 

I just did a drive by today and noticed my tenant is storing an excessive amount of household items in the yard, including indoor furniture. 

So if you're investing in multiple deals, you'll need to gain some understanding of the markets, review sponsor track records, verify their financials projections make sense and that they're using reasonable assumptions, make sure the fees aren't excessive (fees vary for each deal).

It absolutely was a win/win: Taxes went down well in excess of the fee charged.