All I can tell you is this same question gets asked over and over again and the answer is to avoid the decisions and properties that create turnover.

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Avoid carrying a clip board otherwise people are more hesitant to open the door.

Do I itemize in hopes that he will see the extent of damages (and all the things he isn't being charged for due to the exhaustion of his deposit), and hope to avoid additional issues with this family?

I like to make sure that the house is up to date on electrical and plumbing, as well as avoiding possible surprise costs. but would rather find more investors and find quality deals at a steady rate.

I've also found that when I run a credit check many who have a fair number of accounts over 30 days in arrears (even if they haven't reached the collection stage) are to be avoided over a concern they've become too casual about living like this and thus adding another notice of a late fee (or even a threat of an eviction) doesn't seem to bother them very much.Gail

You could also sell property #1 within the next 4-5 years and avoid paying capital gains= more money to invest with. 

But perhaps it is better to purchase the home outright to avoid the interest that comes with a mortgage.We also currently have two mortgages and will be buying a primary residence in another three years.  

.- Avoid agents that have been doing it a while, but that aren't sourced via referral.

If you ever gain a partner, you can then use that same EIN to file your partnership taxes.Since it's cheap and easy, get the LLC setup out of the way from the start, and you'll avoid all the questions you asked down the road.Oh, since DeuterInvestments.com is still available, and you've mentioned it publicly, I recommend purchasing it asap before some squatter grabs it.