That’s a legitimate strategy and I commend you for maintaining a high standard and going after a better quality of tenant but you must know and be aware that you are limiting yourself to The top 15-20% of the entire rental market which is going to make it much harder to fit that criteria .

Because this legitimate inconvenience can be repeated with any  other tenant.

There are definitely more deductions available when an investor becomes a legitimate business.

The former tenant has a good job of over 8 years with a telecommunications company.I'm just afraid to sign a contract with a collection company and then find out I've done the wrong thing and I'm tied up with them but they're not legitimate.     

Because the preparer doesn't audit prior to tax prep, we really don't have any way of guaranteeing that there's a real, legitimate business operating out there.But by stating "client represented and I prepared the taxes indicating...." that's really all I can attest to. 

I have a buddy that's doing it himself and providing an excel sheet to a legitimate accountant.

There are legitimate reasons to structure this way, but every dollar you pay yourself as property manager is subject to 15.3% self-employment tax  if you are turning around and reducing your S Corp income so that you minimize SE taxes, you should have just left it as passive income to begin with   What was your goal here?

As long as the property value is legitimately going down, or going up slower than it would otherwise, it seems like it would be a punishment to not be able to write off $13k per year, since there is a -$13k per year drag on the property value. 

Additionally, striking the right balance between protecting property owners and allowing for legitimate wholesaling activities poses a complex challenge for regulators.Conclusion:As the real estate wholesaling industry continues to evolve, state legislatures and regulators are actively working to establish a regulatory framework that safeguards the interests of all parties involved.

And please know, I am asking legitimately with interest in the answer, not confrontationally as many people like to be on these forums.