I made sure to point out that conventional financing would likely lead to a waste of time and additional work on his end, and he understood because he held many properties.

If you have experience with it, would love to hear your thoughts, but that's not my main question.I was looking into an Health Savings Account (HSA) which looks like a great option as well for minimizing medical costs (since most non-premium payments can be deducted via an HSA) but You must have a high deductible health insurance plan to qualify for an HSA. 

Would prefer to know if I'm wasting my time and 500 bucks to file. 

If you have him coming out and bidding tons of projects for you, but aren't giving him any work, he will definitely start to realize you are wasting his time and may be upset, so keep that in mind too. 

and many times you will find your waste line is contaminated and needs to be snake ( easiest if able) or is beyond useful life and needs to be replaced

I’m hoping to sell it and walk away with breaking even or paying a very minimal amount..

Let me count the ways:1) Licensing and Entity Set Up2) Establishing Proper Bank Accounts3) Creating a Phone System 4) Having no PM education or experience5) Accounting6) Marketing - Of themselves and the homes they manage7) Application handling with screening8) Lease execution - minimal understanding of how to fill in a lease9) Tenant laws and regulations10) Tenant relations11) Maintenance (I should say that 5 times)12) Make Ready issues13) Security Deposit Itemizations (the most expensive failure you can quantify)14) Failing to seek advice or education 15) Service Animals16) Fair HousingI could go on, but one of the biggest and would considered the "umbrella".....is not providing a quality service to their owners and tenants. 

Better to off load the property than waste spending good money after bad.

I did not read it and will not waste my time on it. 

It's a lot of liability for the employing broker with minimal return so it's just a hard pitch for you to make.