I've seen landlords live in blissful ignorance for 5-10 years due to dumb luck, then their world comes crashing down and they lose everything.I have a book, there are some in the BP bookstore, or you can check out one of my personal favorites, Every Landlord's Legal Guide by NOLO.

But need to check legality of that.

My point is cash has no exclusivity on being legally clean and far from it.

I have done extensive research in the risks, how to structure such deals to mitigate those risks as effectively as possible, and legal considerations of each strategy. 

I prefer graduate students whenever possible because they don't have time for partying, are of legal age anyway, and generally tend to be by themselves or with a partner so it's more like renting to a couple.

Trying to pay the least amount of taxes legally possible. 

I consulted with a real estate lawyer a few times this year who said it's very hard to sue for negligence and they advised against taking legal action, especially since the property manager at least followed through on the eviction and repairs.I've now asked the property management company to apply a $4k credit for all the challenges I've had working with them.

Even if they do not, it’s not your legal responsibility.Long version: It actually depends on your method of payment, and it’s not always clear.Credit card payments: clearly not you problem, no 1099s needed.Zelle payments: you DO need to send 1099s for Zelle payments.PayPal, Venmo and Cash App payments: this is where it gets tricky.

Quote from @Shaun Ng: Hi, I recently have a legal name change, and I own 2 rental properties in Fairfax county, VA.

The lender even quit communicating with me, which I did not think was legal.