Clean and private is the only part I would spend money on. 

The hardest part is getting good deals.  

Early preforeclosures are not ready to admit they are even behind, they still think they can dig their way out and often times, all parties in the house don't even know about it.

If they  reached the level of noise where it where it would be a neighborhood problem  (e.g. were throwing parties every weekend) I would tell the complaining tenant to call the cops and would try to get the partying tenant out on a lease violation. 

For 2020 forward, the form is actually 1099-NEC.File if you make payments of $600 or more for services, in the course of a trade or business, to independent contractors in any combination of cash, check, e-check, and certain third party payment platforms.Payments to a corporate tax entity -- C or S -- generally do not require a 1099, unless the payment is for legal services.Most rental owners who employ PMs shouldn't be issuing a lot of 1099s. 

I went to AA for grad school, and have been in that house for a few parties! 

I think in general these type of non-conforming units are better used for house hackers who have the opportunity to develop a closer relationship with their renters than somebody who is buying an investment property that will be managed by a third party.

Namely, when using a 3rd party property management company, do I need to account for the tenant security deposit on *my* balance sheet?

If I am a newbie, what would give the owner the security of knowing the transaction would be beneficial for both parties?

As much as I'm all about FIRE (or at least the FI part), I do not believe that I can contribute 100% pre-tax and ultimately convert at 0% over time based on my individual situation (my buddy on the other hand who is planning to do this is in a different situation and it's POSSIBLE, but in my opinion not PROBABLE long term).