Do I hate my money or is this a legitimate concern?

Sounds like you would be well advised to find full employment somewhere and build your credit, some money while still actively looking for RE.I've never heard of legitimate investors in RE that got rich quickly.

Most of us on this forum agree, and Arron stated as much, that not every program or every seminar weekend or home study course or 'Guru" pitch is legitimate or even useful, but there are a great many that are very good.

As a pass-through entity, there are no particular tax benefits except that it helps to fend off an IRS audit by showing that you run a legitimate business and all those deductions you claimed were legitimate, but ONLY IF YOU KEEP GOOD BUSINESS RECORDS and do all those things above like write checks and operate like a real business.

It may be the security deposit was very little and not worth pursuing or the security deposit may have been legitimately used to cover the landlord's expenses for cleaning and damages, or even unpaid rent, unpaid utilities, and unpaid fees.  

Within a few hours (Wed Afternoon) I had two agents on the phone pulling quotes and verifying if their insurance partners provided the item I need.TL:DR - I have my quote from the local agent (check), I'm actually saving money (check), my pm is satisfied (check), and I'm now looking forward to the 1st round of rent collection.And yes, my PM provided the exact same example.Follow Up: what's the best way to indepenantly verify the insruance policy you have is 1) a real policy 2) actually legitimate? 

Just to be sure everything is filed correctly.I've been trying to find a legitimate Registered Agent company for out of state LLCs, if anyone comes across a good company, please let me know.

One super important thing that I rarely see discussed when this question comes up is this: If you do form a LLC and take the property in that entity (whether directly or by quitclaim deed shenanigans), make sure you legitimately treat your LLC's operations as separate from your own personal financial operations.

I would get an attorney- go after the broker (if it was legitimate I could), and go after the borrower.

This is often not the case.Moving deductions into future years is a legitimate tax strategy in the right circumstances, but it takes a multi-year analysis.